The Operations Room: A Podcast for COO’s

In this episode we discuss: How do you build an organisation to compete with Google? We are joined by Omid Ashtari, ex-COO of Streebees and President of Citymapper.We chat about the following with Omid: How do you think about organisational structure? How proactive should you be in anticipating organisational challenges? What is the highest impact communication challenge you helped resolve? How do you prevent drift from the customer as the company scales? References: http://www.linkedin.com/in/ashtarihttp://www.startuppragmatism.comBiography: I have two decades of experience in tech and worked in sales, business development and strategy roles for Google across the Dublin, London and San Francisco office during his 7 years there. As the first international employee, I set up Foursquare in Europe as Managing Director. I subsequently joined Citymapper for 6 years as President running the non-engineering side of the business. I then joined Streetbees as COO running operations, international expansion, finance and legal. Throughout my career I have raised north of 100 million dollars of funding for businesses I have worked for.I am an angel investor in more than 45 businesses and advise many of them in all manner of things including strategy, operations, business development, fundraises etc. I am also part of the Mayor of London's Business Advisory Board, and a Mentor at Seedcamp and Entrepreneur First.I am also an aspiring writer for my blogs startuppragmatism.blog and thefullspectrum.blog.Summary:Personal growth and evolution over 13 years. 0:05Brandon reflects on his past solo travels and how they relate to his current life.Brandon M reflects on his past self-absorption and lack of empathy, now prioritizing supporting others' success and empathy in personal and professional life.Brandon M recounts a 2011 incident where he carried a biscuit tin full of Canadian coins and sat next to a homeless person, now recognizing the importance of empathy and caring for others.Organizational structure and skills for a business. 4:09Bethany: People often create an org structure that prioritizes making their existing team happy, rather than starting fresh and building a structure that works for the business.Brandon M: Bethany suggests starting with a blank slate and building an org structure that works for the business, rather than trying to fit existing team members into a pre-existing structure.Bethany and Brandon M discuss the importance of defining the skills needed for a business to succeed, rather than simply morphing structures around people.They agree that it's better to have a flexible approach to organizational structure, recognizing that roles may evolve as the business grows and changes.Organizational design and hiring for a scaling startup. 9:57Brandon M. faced pushback on hiring 2 product marketing managers, but believes it was necessary for success in both self-serve subscribers and enterprise sales.Brandon M. emphasizes the importance of clear go-to-market strategy and collaboration between product marketing manager and go-to-market manager.Bethany identifies the need for a "thinker" in early-stage businesses to analyze and gather information, which is perceived as a luxury role but essential for product market fit and growth.Bethany highlights the importance of having a thinker and a strategic salesperson in a scaling organization, as they provide valuable insights and help navigate challenges.Bethany identifies signs of organizational design issues, including unhappiness, confusion, and a lack of managers or promotional opportunities, which can lead to restructuring.Organizational structure and scaling. 16:27Omid Ashtari discusses the importance of adapting organizational structure to the scale of the problem being solved, as the number of employees grows.Ashtari highlights the challenges that arise when an organization expands, such as natural breaking points and lines of communication, and the need to adjust operational systems accordingly.Communication and decision-making challenges in scaling startups. 18:37Omid Ashtari explains how companies can proactively address problems by embracing chaos and redesigning systems after hiring new employees.Omid Ashtari highlights the importance of clear communication and decision-making processes in startups, particularly in scaling businesses.He shares an example of a company experiencing success bias, where they lose humility and become less secure, leading to bottlenecks in decision-making and communication.Product-market fit and organizational structure for startups. 22:39Omid Ashtari highlights the importance of addressing user complaints and recalibrating employees' understanding of the product's performance in different cities.Citymapper encourages engineers and employees to travel to different cities for exploratory trips to better understand user needs and improve the product.Omid Ashtari discusses the importance of understanding customer needs and maintaining product-market fit in scaling startups.Hiring for various roles in a business, focusing on cognitive ability and adaptability. 26:49Omid Ashtari discusses the importance of hiring the right person for the job, particularly in scaling problems, where high roller related knowledge is crucial.Ashtari highlights the challenge of figuring out the business model for a problem like city mapper, where role related knowledge is less important than adaptability to the organization's synchronous ease.Omid Ashtari emphasizes the importance of hiring people with high cognitive flexibility and entrepreneurial mindset for a specific business unit within a company.He describes a cross-functional team structure where team members sit in different rooms and communicate ad hoc to solve problems quickly, with a central table for impromptu meetings.Scaling a transportation app company. 32:26Omid Ashtari emphasizes the importance of adapting to changing business needs by creating separate units with different operating systems to address specific problems.In Citymapper's case, the main focus was on retaining organic growth in London, with a myopic focus on product innovation and weekly updates to address user feedback.Omid Ashtari describes the challenges of scaling a transport app, including competing with Google Maps and Apple Maps, and the need for a sustainable business model.Ashtari highlights the importance of resilience and entrepreneurial spirit in overcoming these challenges, and the need for tooling to enable non-engineers to launch cities.Entrepreneurship, product market fit, and organizational design. 37:48Omid Ashtari emphasizes the importance of asking questions and reorganizing as needed in the face of uncertainty.Citymapper's team has adapted to changing needs by reassigning personnel and launching new initiatives like smart ride, a cab-based ride-sharing service.Omid Ashtari emphasizes the importance of being "confidently insecure" as an entrepreneur, constantly reassessing and adapting to changing circumstances.Bethany agrees, highlighting the need to be emotionally intelligent, flexible, and humble in the face of uncertainty and criticism.This podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy

Ex-COO of Skyscanner, Mark Logan, discusses scaling from 100 employees to IPO. Topics include foundations of scale, preventing command and control, issues with organisational alignment, why OKR cascading fails, golden processes of an organisation, challenges of scaling, innovation process, going cross-functional, expectations from C-level roles.

In this episode we discuss: What can VC and PE backed operators learn from each other? We are joined by Sam Smith, the founder & MD of PepTalks, a training provider for private equity backed CEOs and their management teams.We chat about the following with Sam: What are the types of PE companies? How are company valuations determined? How does the commercial model work between PE companies and LP’s? Can you shift track and move from VC-backed to PE-backed? How does a PE firm structure funds when they invest in an organisation?How does that structure impact the ability for the management team to make money?  How do share options work in VC-backed companies? What happens to the management team's equity when a second PE company buys the company? What does a successful COO look like in PE-backed companies? How does that contrast versus VC-backed?  How do VC-backed companies successfully ramp up headcount so quickly? How do you engage and motivate employees in PE-backed companies versus VC-backed? ReferencesSam SmithPepTalksBiography: Sam Smith is the founder of PepTalks, a peer to peer training provider for private equity backed CEOs and Management teams. Founder of Marble Hill Partners an exec search and interim management consultancy which was sold to Henley Insights Group in September 2021.Summary: Career relevance and identity after unexpected death. 0:05Bethany struggles with processing unexpected death of a friend, leading to a difficult weekend.Bethany and Brandon discuss feeling less relevant in their careers as they age, with millennials taking over management positions.Identity, ambition, and financial freedom. 3:35Bethany: Realized identity wasn't tied to work after leaving peak role, causing discomfort & self-reflection.Brandon: Ambiguity of mattering in work life vs. personal identity, with age & finite time, leads to essential questions.Bethany and Brandon discuss the importance of financial freedom and its impact on their lives, including the ability to think long-term and prioritize personal growth.Brandon highlights the importance of allocating time for networking and learning, even when not directly relevant to work, to maintain personal direction and growth.Entrepreneurship, private equity, and networking. 9:02Bethany and Brandon discuss networking and success in business with Sam Smith of pep talks.Private equity fundraising and investment strategies. 11:07Sam Smith explains the commercial models of private equity, including the need for return on investment and the importance of valuation based on EBITDA multiples.Bethany asks about the recurring revenue of a 20-500 million enterprise value business, and Sam provides examples of private equity funds for different transaction sizes.Sam Smith outlines a plan to raise £500 million for a private equity fund, highlighting the importance of having a clear investment strategy and track record of success.The fund aims to secure commitments from 20-30 institutional investors, with the remaining £450 million coming from the general partners' own pockets.Private equity investing and expectations. 16:12Sam Smith and Bethany plan to manage a private equity fund for 10 years, investing and returning money to investors over that time.The fund will have a lifecycle of 11 years, with 3-5 exits within the first 5 years, and then raising another fund in transition.Brandon: Has seen venture-backed companies transition to private equity ownership, but rare due to cash generation and profitability requirements.Sam Smith: Private equity investors expect at least a two times return, unlike venture capital which takes a higher risk for potential astronomical returns.Private equity investing and debt structures. 20:41Management teams in private equity firms can make significant sums of money if they deliver growth and meet targets, while VC firms have a higher risk of failure and lower potential returns.Sam Smith discusses raising £500 million for private equity deals, with £40 million going to banks or debt funds and £59 million structured as a loan note with compounding interest.Smith explains the importance of capturing senior debt and structuring loan notes to minimize interest payments and maximize returns.Private equity investment and returns. 25:33Sam Smith explains how private equity firms structure deals to incentivize management teams, typically offering a sliver of equity worth 10-20% of the total valuation.Four years later, the business has grown EBITDA, improved its multiple, and paid down some senior debt, increasing the valuation to 170 million.Sam Smith explains how private equity firms can generate returns through investments, highlighting the importance of valuation and cash generation.Brandon expresses interest in joining private equity, but Sam cautions that returns may not be stellar and management equity may erode in value.VC-backed business growth strategies and employee incentives. 29:37VC-backed businesses prioritize market creation and share options for management teams.Bethany explains that employee stock options are typically structured as a percentage of salary with a vesting schedule, and employees must exercise their options within 90 days of leaving the company to avoid paying the strike price.The strike price varies depending on the set of shares or option grant, and employees must decide whether to hold onto their shares or pay the strike price as part of the sale.Private equity investing and leadership. 33:34Bethany and Sam Smith discuss the importance of vesting for management teams in private equity deals, with Bethany highlighting the need for incentives and Sam Smith explaining the benefits of rolling equity into subsequent transactions.NewVoiceMedia raised money every year, with a focus on deploying and returning funds in a 3-5 year cadence.Bethany: Valuation increases with each funding round, providing opportunities for early investors to cash out or continue investing.Sam Smith: Private equity firms look for entrepreneurial leadership teams with strategic strength and psychological resilience to drive growth and capture market share.Private equity talent acquisition and growth strategies. 38:51Sam Smith emphasizes the importance of operational expertise in CEO candidates for a mid-market company.Private equity firms often overlook experienced VC executives as potential hires due to cultural fit concerns.Private equity firms prioritize hiring experienced executives for faster growth.Talent acquisition and onboarding in private equity firms. 44:33CEO emphasizes importance of talent acquisition and onboarding to ensure aligned focus on value creation.Entrepreneurship, strategy, and talent acquisition. 46:06Venture businesses struggle with identifying and sticking to focus due to market disruption and entrepreneurial excitement.Bethany and Sam discuss talent acquisition strategies for scaling startups, including building a talent team, leveraging referrals, and preparing managers for growing teams.Setting up new managers for success. 49:18Brandon emphasizes the importance of effective line management to ensure new hires are set up for success.HR strategies for scaling businesses. 50:30Bethany emphasizes the importance of investing in L&D and people analytics to improve manager performance and DEI.Sam Smith notes that venture-backed businesses are stronger in HR function, with a focus on people strategy and organisational design.Incentivizing and engaging employees in private equity-backed companies. 52:46Brandon emphasizes the importance of efficiency in talent acquisition and onboarding, highlighting the need to balance rigor and speed to ensure the right candidates are hired.Sam Smith and Bethany discuss the value of analytics in private equity, particularly in understanding employee dynamics and incentivizing employees in PE-backed companies.Brandon: How do PE-backed companies incentivize talent? Sam Smith: Use a similar model to engage employees, educate them on PE ownership, and create a sense of purpose.Sam Smith: Private equity vocabulary can lose engagement quickly, so use language that resonates with employees and emphasizes the business's impact on society and community.Sam Smith emphasizes the importance of purpose and emotional engagement in business, citing private equity's focus on incentivizing and equity for management teams and employees.Sam believes private equity should expand their talent pool beyond traditional sources, including the venture world, to uncover great talent.This podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy

In this episode we answer the question: How do you build a business that is smarter than you? Our guest is Jennifer Sundberg, the co-CEO of Board Intelligence and author of Collective Intelligence.We discuss the following with Jennifer: Why is it so hard to get great conversations in business review meetings? How do you get good at asking the right questions? How do you develop the habit of asking good questions in the organisation? How do you create phenomenal meetings? How do you cut through obfuscation of underperformance when it comes to KPI’s? What are the two types of conversations in management meetings? Are written documents the elixir for creating better meetings? ReferencesThe Collective Intelligence BookBiography: Jennifer is the founder and co-CEO of Board Intelligence, a mission-led technology firm that helps transform boards and leadership teams into a powerful driver of performance and a force for good.Jennifer has won numerous awards, including EY Entrepreneur of the Year for London & South East and The Times Young Business Woman of the Year, and has held regular columns with Management Today and the Financial Times.Together with co-CEO Pippa Begg, Jennifer has authored a book published in November 2023, titled ‘Collective intelligence: How to build a business that’s smarter than you are’.Summary: Using electric currents for beauty. 0:05Bethany Ayers discusses her concerns about her appearance, particularly the jowls and lower face area, and how she has been using microcurrent therapy to address these issues.Brandon Mensa responds to Bethany's concerns and provides his own thoughts on the topic, including his belief that face exercise is important for maintaining a youthful appearance.Bethany discusses her use of electric currents on her face to reduce the appearance of jowls and improve her appearance, despite being a feminist who questions the societal pressure to conform to beauty standards.Bethany mentions the zip Halo, a product she uses for its anti-acne and nano current features, which she believes have helped reduce her breakouts and improve the appearance of her skin.Effective questioning and meeting strategies. 5:20Bethany highlights the importance of asking simple and open-ended questions that encourage critical thinking and problem-solving, rather than complex and leading questions that can limit the conversation.Brandon shares how he has shifted from a more directive and challenging approach to a more curious and why-focused line of questioning, which has led to better results in his conversations.Bethany prefers meetings with a clear purpose and aligned attendees, avoiding unnecessary or unproductive gatherings.Bethany suggests opening meetings with a clear agenda and checking alignment among attendees to maximize productivity.Effective meeting practices and pre-reads. 9:52Bethany and Brandon discuss the importance of periodically reviewing the purpose and format of meetings to ensure they remain useful and productive.Preparing pre-read materials for substantial topics to be debated in leadership meetings can help align everyone and lead to better decisions.Bethany highlights the importance of clarity in pre reads, emphasizing that without it, people may interpret the document differently and have a harder time having a productive conversation.Brandon agrees and adds that pre reads can be used for more than just making a decision, such as for awareness or understanding the background of a topic.Improving board meeting quality through skills development. 14:11Jennifer Sundberg highlights the importance of critical thinking, communication, and focus on what matters most in board information.She emphasizes that these skills are not unique to boards and have far-reaching implications for management teams and organizations as a whole.Asking the right questions in a structured manner. 16:21Bethany and Jennifer discuss the importance of asking the right questions in a framework, with Bethany sharing her experience of iteratively refining questions over time.Jennifer Sundberg suggests using a set of pre-defined questions, called QDs, to help employees think critically and structure their thoughts before writing a report or presentation.She recommends limiting the number of major questions to 5-7 to maintain clarity and avoid overwhelming the receiver with too much information.Improving performance reports by asking simple yet effective questions. 19:25Jennifer Sundberg highlights the importance of addressing the "so what" question in performance reports, as it helps to identify the risks and opportunities on the horizon.Bethany shares her experience of working with teams who struggle to provide meaningful commentary on data visualizations, despite the importance of contextualizing the information.Jennifer Sundberg shares a story about EasyJet's CEO Carolyn McCall, who prioritized employee well-being by asking "how do our people feel?" in every meeting and report, shifting the organization's focus to people and ultimately improving profits.Effective questioning in meetings and leadership. 23:37Jennifer Sundberg emphasizes the importance of asking the right questions in meetings to ensure accountability and precision.She suggests using a software platform or knowledge management system to cascade questions across the organization and update them easily.Jennifer Sundberg emphasizes the importance of asking questions in meetings to encourage open conversations and address underperformance.Bethany raises concerns about politics and lack of clarity in meetings, and suggests addressing cultural issues to facilitate open communication.Leadership meetings and their differences. 29:01Brandon observes that a casual coffee chat with colleagues leads to more open and organic discussions, resulting in valuable insights and revelations.Jennifer suggests grouping agenda items into steering and supervisory categories, with separate meetings to accommodate different modes of thinking and responsibilities.Effective communication through visual aids and self-explanatory reports. 31:42Bethany raises an issue with the assumption that reports must be written in prose, citing her own dyslexia and preference for visual aids.Jennifer agrees, emphasizing the importance of preparing self-explanatory materials that can stand on their own without a verbal narrative to support them.Jennifer Sundberg emphasizes the importance of critical thinking in report production, suggesting that the process of creating these documents can lead to valuable insights and improved outcomes.This podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy

Exploring the challenges and benefits of hybrid working, focusing on inclusivity issues for women and marginalized groups. Discussing trust, leadership, and DEI concerns with industry expert Brian Elliott. Embracing inclusivity and diversity in remote work, addressing CEO challenges and strategies for promoting belonging and growth.

Exploring the COO role in private equity, evaluating employee motivation, board meetings in PE-backed companies, and compensation approaches. Discussion on the title COO versus CRO or CCO, evaluating by PE investors, and the importance of company purpose and leadership engagement.

In this episode we unpack the topic of: Do product leaders make good COO's? with Martyn Fagg, COO of Tillo and Matt Jones COO at ex-COO at ParentPay. Bethany and I discuss the following: What does a good product leader look like? What does a good product manager look like? We then discuss the following with Martyn and Matt: How did the transition to COO happen?Was picking up the people function challenging? How do you get the people function to be more data-driven? How do you get product development and commercial to learn from each other? What product development KPI should be included in the company dashboard?ReferencesThe Speed of Trust: The One Thing that Changes Everything The Four Foundations of SaaS Biography: Martyn Fagg is a seasoned CTO with 20 years experience in software engineering and fintech leadership - passionate about fostering innovation, collaboration, and continuous learning. Currently COO at Tillo, a B2B embedded rewards & incentives platform working with some of the world’s top brands to deliver real-time digital gift & prepaid cards.Matt Jones recently served as the Group Chief Operating Officer at ParentPay, a leading provider of payments and MIS solutions for schools in the UK and Europe. He joined the company in 2017 and initially held responsibility for Product Management, Software Engineering, IT, Service Operations, Customer Implementation, and Customer Support across several early Group businesses (ParentPay, Schoolcomms, Cypad, WIS, and nimbl). Additionally, Matt oversaw the group Security function, ensuring the protection of the company's and customers' data assets.Prior to his tenure at ParentPay, Matt briefly served as COO at IRIS Software. He also spent six years as Senior Vice President of DevOps at NewVoiceMedia (acquired by Vonage) and held previous roles at Mimecast and MessageLabs (acquired by Symantec).Summary: Product development in CEO role with Twilio and Parent Pay leaders. 0:06Brandon and Bethany discuss their cultural heritage for a school event, with Brandon dressing as a tech bro from Silicon Valley and Bethany dressing as a Canadian with a hockey jersey and maple syrup.The hosts joke about stereotypes and cultural representations, with Brandon accidentally saying "boot" instead of "boot" and Bethany pointing it out.Brandon M. questions the importance of good product leadership, emphasizing the need for a clear product vision and strategy, as well as effective team building.Martin Fag, Matt Jones, and Brandon M. discuss the role of product development in the CEO role, with a focus on product leadership, strategy, and team building.Product leadership and CEO roles in tech companies. 4:50The CEO and product leader roles require different skills and perspectives, with the CEO focusing on the overall vision and strategy, and the product leader translating that vision into a tangible product.The product leader must be empowered to take ownership of the vision and make it a reality, while the CEO can evolve their role to focus on other aspects of the business.CEO and product leader have different visions for product strategy, leading to potential conflicts.Product management and leadership. 8:51Brandon M highlights the importance of product managers understanding users, market dynamics, and stakeholder management to ensure a product's success.Bethany agrees, noting that product managers often focus too much on technical details and not enough on validating with customers and stakeholders.Brandon M discusses Marty Kagan's philosophy of product development, emphasizing the importance of empowered teams with autonomy, resources, and scope to solve problem areas.Bethany agrees and adds that being given a problem to solve, rather than features to build, is crucial for product development teams to make a difference.Product management and CEO roles. 13:39Bethany and Brandon discuss the role of a good product person and CEO, with Bethany highlighting the importance of being able to pull oneself up and out of the weeds.Martin fell into the role of CEO as an opportunity after growing the company from six to 50 people and wanting a new challenge.Career progression from CTO to CEO. 16:12Matt Jones describes adaptability and willingness to take on new roles as key to his success as CEO.Leadership roles and responsibilities. 17:38Bethany shares her experience of being the only woman in a male-dominated leadership team and feeling like she's often overlooked or undervalued.Leadership roles and responsibilities. 18:56Martin, a former software developer and CTO, now CRO, has been managing people for 15 years and enjoys the people side of things, working closely with Briney, VP of people.Martin took on the people function as CRO, bringing a unique perspective as he has the largest proportion of the company reporting into him, and he works closely with the executive team to bring a commercial and business perspective.Managing people and teams in a cross-functional environment. 21:53Matt Jones highlights the importance of managing people as individuals, not just roles, in a cross-functional organization.Using data to inform people policies in a business setting. 23:18Matt Jones and Bethany discuss the importance of data in people policies, with Matt agreeing that data can provide insights into people's performance and wellbeing, while Bethany struggles with getting people teams to own and use accurate data.Both Matt and Bethany agree that there needs to be a clear owner of people data, such as a business ops team, to ensure accuracy and better decision-making.Data governance, culture, and retrospectives in a company. 26:22Martin emphasizes the importance of data-driven decision making in people operations, with a focus on employee happiness and retention rates.Brandon and Martin discuss the importance of collaboration and continuous learning within the product development team, with a focus on embedding retros and learning outside of product.Martin highlights the need for a champion within the team to drive initiatives and ensure ongoing adoption, with regular check-ins and feedback to gauge effectiveness.Using "5 Whys" to identify root causes of problems in business. 30:05Matt Jones shares his experience with using retrospectives to drive improvement in teams, emphasizing the importance of psychological safety and a simple five whys process.He faces challenges in implementing retrospectives across different functions and cultures, citing a lack of buy-in and psychological safety.Product-dev collaboration, agile methodologies, and software engineering. 32:19Bethany and Martin discuss the challenge of different departments within a company not sharing knowledge and resources, despite being in the same industry.Martin and Matt discuss the challenges of measuring productivity in software development, with a focus on the differences between short-term and long-term goals, and the need to prioritize creativity and outcomes over process productivity.Matt argues that software engineering is a creative undertaking, and that agile methodologies can help align development with personalities and produce better outputs by focusing on outcomes rather than in-process productivity.OKRs, product development metrics, and trust in the CFO-CEO relationship. 36:11Brandon M suggests cross-functional OKR teams can foster cross-pollination and inspire company-wide collaboration.Martin agrees on the importance of measuring developer productivity, citing deployment frequency and ticket turnaround time as key indicators.Martin emphasizes the importance of security and stability in a business, while Matt Jones stresses the need for speed and delegation of authority to achieve autonomy and purpose.Martin emphasizes the importance of transparency and earning trust from the CEO, citing his experience working with a founder who is hesitant to let go of their baby.Matt Jones highlights the need for a mature and open relationship between the CEO and CFO, allowing for flexibility and adaptability in navigating challenges.This podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy

In this episode we unpack the topic of: How do you tame a visionary CEO? with Rob Liddiard, B2B SaaS Founder (acquired 2022); Reformed Lawyer.Bethany and I discuss the following: Forecasting in 2024Simplifying performance managementSurfacing issues in leadershipDocumenting the processes of the companyWe then discuss the following with Rob: Is the Entrepreneurial Operating System (EOS) just another OKR styled book? How do you tame a visionary founder? What are the components of EOS? What are the two principal roles in EOS? What can experienced operators learn from EOS? How do you achieve an L10 meeting? Referenceshttps://www.eosworldwide.com/rob-liddiardBiography: I previously founded a software company called Yapster. Although we had 100,000 licensed users, amazing customers like Next plc, Brewdog, Krispy Kreme and Caffe Nero and the business looked healthy to outsiders, we secretly struggled internally to execute plans and hit our financial goals. I worked and stressed 24/7. I was a qualified Corporate Lawyer and experienced Businessperson, but I didn’t feel a success. All I could feel was the underlying tension in my leadership team and investor base.Then I read Gino Wickman’s Traction and it was like someone turned a light on. I realised that I hadn’t been leading my organisation to its potential. By adopting EOS’s simple habits and frameworks we quickly achieved Traction. Suddenly I was more successful at work and more relaxed at home.In late 2022 I sold Yapster to a company backed by Google. I’ve since qualified as a Professional EOS Implementer® and now my personal Mission is to help other UK business owners achieve their goals more quickly, with less frustration.Summary: Golf inclusivity and personal experiences with the sport. 0:06Bethany Ayers and Brandon Mensa discuss golf and inclusion with guest Rob, with Ayers sharing her experience at a virtual driving range and appreciating Rob's proactive approach to inclusivity.Bethany Ayers shares personal experiences with golf and her grandfather's intense passion for the sport, despite exclusion of women in the family.Entrepreneurial operating system and vision alignment. 4:18Brandon: Book provides a prescriptive set of steps for non-experienced companies to run their businesses efficiently.Bethany: Book offers a structure for strategy days, with exercises and time allocations for each area, saving time and effort.Bethany Ayers discusses the importance of aligning to a vision and creating a three-year plan, with regular revisions to ensure accountability and profitability.Ayers highlights the challenges of budgeting in a changing world where cash is no longer free, and the need to focus on cache management across multiple years.Simplifying performance management systems. 10:21Brandon and Bethany agree that the "right people in the right seats" framework is simple and effective in evaluating employee performance (10 words)Traction recommends using a scorecard and weekly pulse to track leading indicators of KPIs (20 words)Bethany Ayers emphasizes the importance of tracking key metrics, such as ticket clearance times and pipe Gen, to identify and address issues in a timely manner.She believes that having a weekly scorecard with 5-10 metrics can help the team stay disciplined and proactive in addressing problems, leading to better customer experiences and overall success.Leadership, processes, and accountability in a business setting. 15:09Bethany Ayers highlights the importance of understanding the interconnectedness of different functions within a company, and how this knowledge can help resolve issues more effectively.Brandon emphasizes the value of documenting processes between functions to avoid siloed thinking and improve collaboration.Brandon and Bethany discuss the book "Traction" by Gabriel Weinberg, which emphasizes the importance of meetings for accountability and using OKRs (Objectives and Key Results) to set goals.Rob Leyard, CEO of Eos, shares his "come to Jesus moment" when he realized the importance of operations after almost failing due to neglecting it.Challenges with global rollout of software product. 20:50Rob struggles to explain why his company's global rollout failed despite initial success.Entrepreneurship, leadership, and managing visionary CEOs. 22:30Rob shares his personal story of struggling with his tech startup, including not getting paid for 7 months and experiencing marital problems.Bethany Ayers commends Rob for his honesty and openness, and shares that many entrepreneurs can relate to his challenges.Rob recognizes that working with visionary CEOs can be challenging due to their unique perspective and potential lack of clarity on their company's identity and goals.Rob's approach to taming visionary CEOs involves recognizing the problem, understanding their perspective, and using practical tools like EOS to help them achieve their dreams while aligning with reality.Business strategy and operations for startups. 26:35Rob is frustrated that his business is not growing despite his charisma and support, and he suspects that he may be doing something wrong.The book "Excellent Entrepreneur" provides a framework for businesses to run coherently, with six components: vision, data, process, traction, issues, and people.Brandon and Rob discuss the importance of a clear vision and traction plan for startups, including creating a one-page business plan and setting quarterly strategic initiatives.They also emphasize the need for data-driven decision making and consistent processes across the organization to drive accountability and good habits.EOS framework for entrepreneurs and operators. 31:51Rob emphasizes the importance of identifying and solving root causes, rather than just discussing them.Bethany Ayers agrees and adds that there are two roles in EOS, and taming comes into play.Rob: EOS model requires visionary to identify integrator, who is CIO and essential for success.Bethany Ayers: Using EOS playbook can help find common language between operator and visionary, elevating professional operator to center of organization.Entrepreneurship, EOS, and the role of operators. 36:07Rob, a passionate advocate of EOS, shares insights on how individuals can help visionaries in stuck organizations by taking control of their own careers and self-esteem.Rob suggests creating a personalized explanation of EOS components and how working with Brandon can help organizations move forward.Rob is open to creating his own operating system after finding success with EOS and reading other business books.Rob believes that finding a system that works and elevating operators to their rightful place in the entrepreneurial community is enough for him, and he now preaches the gospel of operation excellence to others.Effective meetings and organizational alignment. 41:13Brandon and Rob discuss creating an L10 meeting, which involves starting with a segue, reviewing rocks, looking at the scorecard, and addressing issues.The meeting agenda includes a fixed agenda, and issues are reviewed and prioritized for solving in the next week or quarter.Rob emphasizes the importance of finding a workplace where you are appreciated and implementing a system to manage growth and issues effectively.Rob encourages listeners to explore different systems and not settle for a company that is happy living in chaos, and to give them the opportunity to come meet them where they are.This podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy

In this episode we unpack the topic of: The COO Role: Why Would You Ever Want the Job? with Chuck Orzechowski, CEO of the COO Forum. Bethany and I discuss the following: How do you avoid being the dumping ground for things that others don’t want to do?  Why would you want the COO job? We then discuss the following with Chuck: What are the most common issues you see across your COO membership? What is the best approach to clarifying decision-making authority with the CEO? Why is “pace of change” a common frustration for COO’s? What do you do when the CEO relationship is not working for you? What is the key criteria for determining a good COO-CEO match? What are the rewarding elements of being a COO? ReferencesThe COO Forum® has been delivering on the mission of helping Operations Executives achieve more since 2004. Our members tackle the most pressing challenges facing their businesses and those that shape their careers. Join the best Operations Executives in the world as we celebrate our 20th Anniversary. Don't go it alone in 2024.Launching this February, Find Your COO™ will provide CEOs/Recruiters a one-stop source for finding talented COOs. The platform is built on top of the CEO-COO Alignment Index™ scoring system. It uses 25 key questions to create profiles for both the hiring CEO and COO candidates. These questions cover areas such as preferred communication frequency, speed of change, role relationship, delegation, trust development and more. Then, both parties can see each other's scoring reports to better assess potential fit or mis-alignment. This sets the stage for improved recruitment, interviewing and alignment post hire, which leads to better performance and COO job satisfaction. Biography: Chuck Orzechowski serves as CEO of the Chief Operating Officer Business Forum® (COO Forum®.) Since 2004, the COO Forum’s mission has been to support operations executives in achieving more in their business and professional lives. As a peer-based professional development organization, the COO Forum has helped 1000’s of executives navigate the challenges of their roles and improve business outcomes. Over the past 28 years, Chuck has spent most of his career leading operations in a wide variety of industries and company sizes, ranging from start-up through Fortune 500s. Chuck has a passion for improving operations, scaling businesses, and the professional development of others. It’s what gets him out of bed each morning...that and coffee!Summary:Whiskey, rock concerts, and personal values. 0:05Brandon and Bethany discuss Bethany's husband's illness and their celebration with whiskey advent calendars.Brandon attends a Danko Jones concert at the Garage in North Islington, describing the band as a fusion of rock, punk, and jazz.Brandon mentions a mosh pit at a concert where he was the "enforcer" to push back, but he was not tempted to join due to his age and past experiences.Bethany has been reflecting on her values and purpose in life, realizing that having fun is her guiding principle, and she's looking for innovative and energizing experiences that bring her joy.Bethany was approached to become a CEO but lacked passion and interest in the domain, leading to her rejection in the final interview.Despite feeling relieved to not have to present, Bethany's lack of enthusiasm was picked up on by the only woman on the board, who ultimately decided not to move forward with her candidacy.CEO roles, delegation, and avoiding unnecessary work. 7:21Bethany shares her realization that she doesn't want to leave her children a large inheritance and instead wants to prioritize their education as their inheritance.Brandon questions the appeal of the CEO role and why Bethany would want the job, given her newfound priorities and interests.Brandon and Bethany discuss how operations professionals can avoid taking on tasks that nobody else wants to do, such as ISO certification or back-office work.Brandon suggests delegating tasks to others or hiring someone to handle them, while Bethany agrees and shares her own experience of successfully pushing off ISO certification to others.Both Brandon and Bethany emphasize the importance of owning your role and delegating tasks to others to avoid taking on too much work that you're not passionate about.CEO aspirations and leadership skills. 13:28Bethany highlights the variety and problem-solving aspects of being a CEO as a source of enjoyment.Bethany desires the CEO role for the authority and accountability it provides, as well as the opportunity for a deep relationship with one person.Brandon enjoys connecting the dots to make a company successful, and he finds it fascinating to analyze data and trends to inform go-to-market motions.Brandon also enjoys coaching others, whether it's helping them rise in their careers or gain confidence, and he finds it both altruistic and selfish.The COO role and its universality. 19:08Chuck discusses the COO role and its universality beyond just tech startups.CEO-CFO relationship, decision-making challenges. 20:41Chuck identifies the top 2 challenges faced by operations executives: misalignment between the CFO and CEO, and scaling the business while dealing with people challenges such as decision making. (20 words)Bethany asks Chuck about the most common complaints and challenges she hears from new members, and Chuck shares his own war stories and insights. (10 words)CEO makes decisions differently than operations executives, with a unique perspective that's difficult for others to understand.Communication is key to understanding CEO decision-making process and partnering with them to offload some decisions.CEO role, decision-making, and pace of change in organizations. 26:09Brandon and Chuck discuss the challenges of decision-making as a CEO, including the need to balance facilitating the leadership team with making decisions as a group.Chuck mentions the importance of documenting the decision-making process to avoid confusion and ensure consistency, particularly when it comes to the pace of change within an organization.Chuck shares his personal story of joining a startup as COO and making changes despite the owner's return from sabbatical.Navigating a business with a non-alignment CEO. 29:47Chuck wanted to analyze financials to understand business growth and make decisions to improve the CEO's life.Chuck saw the profit and loss statement but not the balance sheet or forecast, despite requests, and struggled to align goals and decision-making with the CEO.Chuck emphasizes the importance of communication and decision-making in a CEO-peer relationship, particularly when the CEO's expectations are not aligned with reality.Brandon advises peers to assess their ability to operate in the CEO's environment and make decisions based on their own needs and goals.Leadership hires, values, and styles in business. 34:25Bethany observes that 50% of leadership hires fail, and hypothesizes that this is due to leaders' inability to adapt to different situations and cultures.Chuck believes leadership assessments are less important than alignment in a CEO-CFO relationship, focusing on communication, decision-making, trust, and growth expectations.Chuck is developing an CEO alignment index to help organizations identify the right CFO fit, based on a candidate's desire for change and growth, and alignment with the CEO's vision.CEO role, challenges, and rewards. 38:43CEO matchmaking platform assesses alignment between CEO's preferences and role requirements.Chuck highlights the importance of people skills for COOs, who often serve as a buffer between the CEO and rest of the organization.Brandon asks an unconventional question about the CEO forum, which includes CEOs from various industries, emphasizing the people-based nature of software development and collaboration.Chuck emphasizes the importance of communication and alignment among CEOs and their teams, citing the value of diverse perspectives and missions in driving success.Chuck encourages CEOs to stick with the role, highlighting its rewarding nature and the importance of perseverance in overcoming challengesThis podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy

In this episode we ask the unpack the question of: Do COO's have a two year shelf life? We discussed this topic with Casey Woo, CEO @Operators Guild. We discuss the following with Casey: What is the role of the COO? Why does the COO have a two year shelf life? If that is the reality, how should one think about their career? What does this mean for 4 year option grants? What are the key terms every COO should negotiate? Referenceswww.operators-guild.comhttps://summit.operators-guild.com/2024Biography: Casey Woo is a seasoned multi-stage operator and 7x CFO with over two decades of experience in business operations and finance from investment banking on Wall Street to Silicon Valley tech start-ups. Casey now leads 800+ CFOs, COOs, and Biz Ops company builders as the co-founder of Operators Guild, a community for professionals in strategic finance and operations roles. He believes strongly that community is what makes the difference for start-ups and professionals. When he’s not working, Casey is spending time in California’s Bay Area with his wife and three children. Summary:CEO shelf life and software frustrations. 0:06Brandon and Bethany discuss their least favorite piece of software, with Brandon naming Microsoft Teams as his least favorite and Bethany agreeing due to its poor performance on Macs.Both agree that the entire Microsoft suite, including Word, has always been problematic and frustrating to use.Bethany and Brandon discuss the pros and cons of Google Docs and Microsoft 365 for collaboration, with Bethany preferring Google Docs for its ease of use and collaboration features.Brandon shares his experience of transitioning from Microsoft to Google Docs, finding it difficult to adjust to the new platform but ultimately appreciating its collaboration capabilities.Bethany: Transition from growth to optimization occurs around 50 million in revenue and 250 employees.Brandon: First two phases of growth and commercialization are enjoyable, but third phase of optimization is less enjoyable and happens around 50 million in revenue and 250 employees.Communicating option value to employees and talent acquisition teams. 7:57Bethany suggests using a product like Lecce to help employees understand the value of their options and how they vest over time.Brandon agrees that communicating the value of options as part of compensation is important, and notes that their company could have done a better job of this in the past.Brandon and Bethany discuss the importance of educating employees on option grants and their value, including providing a clear framework for career progression and regular updates on the terms and benefits of option grants.Casey Woo, founder of the Operator's Guild, shares his experience of implementing option grants for employees, including tying them to job role and seniority, and providing awards for top performers to increase their options.CEO role and responsibilities. 12:50Casey Woo shares insights from 35,000 hours of listening and talking to CEOs, highlighting the diverse reasons why people want to be CEOs, including wide impact and not being a CFO or salesperson.Woo challenges the common view of CEOs as a single role, emphasizing the various perspectives and responsibilities held by CEOs in different companies and stages of growth.Casey Woo argues that a CEO's role is not just one person, but rather a complement to the CEO and a gap filler.CEO roles, decision-making, and power dynamics. 16:53CEOs face unique challenges, including rapidly changing roles and delicate power dynamics with other executives.Casey Woo emphasizes the importance of clear decision-making roles and responsibilities in a CEO-founder relationship, avoiding confusion and undermining the CEO's authority.Bethany agrees, citing decision-making power as a common challenge, particularly with founder CEOs, and discussing strategies to address it.Bethany and Casey discuss the role of a CEO in a scale-up company, with Bethany advocating for a two-year vesting schedule and Casey suggesting a step-two approach to becoming a CRO or CFO.Casey emphasizes the importance of understanding the expectations and limitations of a two-year CEO role, and how it can lead to a more successful transition to a permanent position.Stock options in the UK and US, with insights on vesting schedules, taxes, and exercise windows. 24:01Bethany learned that cliff vesting options, where only a portion of options vest after a certain time, was common in the UK 10-15 years ago but is no longer used.Bethany and Casey Woo discussed the challenges of stock options, including high exercise costs, limited time windows, and uneven vesting schedules.Options for early-stage companies in the UK and US. 26:33Brandon and Casey discuss the differences in UK and US options laws, with the UK offering lower strike prices and longer exercise windows.Casey argues that it's employee-friendly for companies to offer longer exercise windows, as early-stage companies need time to reach value.Options negotiation and key considerations. 29:03Bethany and Casey Woo discuss the importance of negotiating options and understanding the terms, including strike price, vesting, and good lever provisions.They emphasize the value of having a clear understanding of these terms to protect one's interests and maximize the potential of options.Equity compensation and career growth for scale-ups. 31:18Brandon recommends revising the Articles of Association to ensure board discretionary ownership doesn't affect an entrepreneur's livelihood.Casey Woo agrees and adds that double trigger or single trigger acceleration of vesting is important for operators and senior operators in the event of a change of control.Casey Woo emphasizes the importance of understanding the stage of a company and its evolution when negotiating compensation and setting career goals.Casey encourages listeners to be realistic about their expectations and to transform and exit the company within a set timeframe, rather than staying for an extended period without achieving goals.This podcast uses the following third-party services for analysis: Podcorn - https://podcorn.com/privacy