
Between Two COO's with Michael Koenig
Between Two COO's brings incredible Chief Operating Officers together to share their insights, advice, and crazy stories. Learn from current and former COO's from companies like Tucows, Automattic, Shippo, Chopra Global, & VC firms.
Latest episodes

Aug 2, 2022 • 38min
Goodworld CEO, Dale Pfeifer on scaling social impact via tech, Mastercard, Citi, & BlackRock's leadership in corporate social responsibility, pandemic's impact on accelerating CSR, pitching President Obama, & more
Dale Pfeifer, CEO of Goodworld, chats on scaling social impact through tech, the evolution of CSR (corporate social responsibility) from consumer targeted to greater corporate involvement, Mastercard, Citi, and BlackRock's leadership in CSR, the impact of the pandemic on accelerating CSR, the challenges of raising VC capital as a woman and as a social impact co., and what it's like to pitch President Obama & being on the front page of the NYTimes.Goodworld helps companies grow by making it easy to embed Social Impact into commerce, workplace culture and sustainability initiatives. Through our Social Impact experiences, sales teams close more deals at higher prices, HR teams increase employee engagement and attract talent, ESG teams drive ROI from their activities, and marketing teams create irresistible brands that boost product prices.Dale Pfeifer is passionate about Social Impact, CSR and ESG. Dale is the founder and CEO of fintech Goodworld - named one of the World’s Most Innovative Companies and a World Changing Idea by Fast Company magazine. Their Social Impact Platform empowers employees, customers and communities to drive positive cultural change together through giving, volunteering and rewards.Goodworld - https://goodworldnow.comDale Pfeifer's Ted Talk - Creating a good world one # at a time Dale Pfeifer on LinkedIn - https://www.linkedin.com/in/dale-pfeiferEpisode Webpage - https://betweentwocoos.com/goodworld-ceo-dale-pfeiferBetween Two COO's - https://betweentwocoos.com Lean Startup - http://theleanstartup.comMichael Koenig on LinkedIn - https://linkedin.com/in/mkoenig514

Jun 14, 2022 • 45min
Bolster EVP, fmr Makerbot CEO & Techstars COO&CIO, Jenny Lawton on Makerbot's $400M exit, running one of the world's most successful seed fund & accelerator, Montessori framework in business, her advice to my daughters & more
Jenny Lawton is the EVP at Bolster, an on-demand executive talent marketplace that helps accelerate companies’ growth by connecting them with experienced, highly vetted executives for interim, fractional, advisory, project-based, or board roles. Prior to Bolster, Jenny served in a variety of C-Suite roles which include her time as the Chief Strategy Officer and then CEO of MakerBot, the leader in desktop 3D printing technology that was acquired by Stratasys for over $400M. Jenny also served as the COO of LittleBits, the STEM learning division of Sphero (the company behind the adorable droid BB8 that captured our hearts in the latest Star Wars films), and then as COO and CIO, Chief Innovation Officer at Techstars, the global startup accelerator which is near and dear to my heart. It’s also worth noting that Jenny was inducted into the Connecticut Women’s Hall of Fame in 2014 for her work in business and labor.And in case you haven’t picked up on it, Jenny has dedicated herself to empowering others to invent and innovate, whether through creating products for makers, empowering startup entrepreneurs, or connecting companies and executives with great opportunities.Jenny Lawton on LinkedIn: https://www.linkedin.com/in/jenny-lawton-09278410Bolster: https://bolster.com/Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 Episode webpage: https://betweentwocoos.com/jenny-lawtonBetween Two COO's: https://betweentwocoos.com

Jun 1, 2022 • 54min
Handshake COO, Jonathan Stull on democratizing access to opportunity, the journey to $100M ARR & a $3.5B valuation, building a three-sided marketplace, timing, global expansion, adding independent board members, the move to hiring specialists, and more
Handshake COO, Jonathan Stull, joins to talk about the journey of building a three-sided marketplace to $100M ARR at a $3.5B valuation with over 500 employees. We touch on the role of COO at Handshake; Jonathan's path from waiting tables to Capital Hill to PE to tech; compromising on tactics but not on vision or mission; adding independent board members; deploying $100MMs in funding; the move from hiring generalists to specialists; global expansion; timing and more.Handshake’s mission is to democratize access to opportunity: to help every student find the right job, no matter where they’re from or who they know.Today, Handshake is the number one site for college students to find jobs. Handshake powers career offices at 1,300+ higher ed institutions—including 100+ community and technical colleges. With 550,000+ employers recruiting on Handshake—from every Fortune 500 company to nonprofits, startups, and more—schools that join Handshake see on average a 3x increase in the size and diversity of their employer network.Jonathan Stull on LinkedIn: https://www.linkedin.com/in/jonstull/Handshake: https://joinhandshake.com/Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514/Between Two COO's: https://betweentwocoos.com/Episode Site: https://betweentwocoos.com/handshake-coo-jonathan-stull/

May 2, 2022 • 30min
GoGuardian COO, Cyrus Mistry, on joining at the same time as $200M in new funding, switching from Google to a startup, how SaaS ops are different than Disney ops, bringing millions of bricked Chromebooks back to life from a cruise ship
GoGuardian COO, Cyrus Mistry, spent 14 years at Google as the Director of Product Management for Chromebooks bringing computers to schools, before joining GoGuardian as COO right when they raised $200M in new funding from Tiger Global Management. Cyrus has a wealth of knowledge not only stemming from his four advanced degrees but also from his operating experience at Disney prior to Google. Have a listen to hear about his story and what it's like to move from Google to a startup.Cyrus Mistry on LinkedIn: https://www.linkedin.com/in/cmistryGoGuardian: https://www.goguardian.comEpisode Website: htps://betweentwocoos.com/gogaurdian-coo-cyrus-mistryMichael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Apr 11, 2022 • 46min
People.ai COO, Art Harding, on Supporting Ukrainian Team Members, E2T: Driving Efficiency, Effectiveness, & Transformation, Translating Chaos & Ambiguity into Structure, How Great Operating Leaders Think Like Project Managers, & More
Art Harding is the COO at People.ai, and joins to share how People.ai has supported their Ukrainian team members, how coaching is inspiring for the right to inspect performance and provide timely and meaningful feedback, the operational mandate of E2T: driving efficiency, effectiveness, and transformation, how COO is the most interesting job in the world, launching new products, what healthy friction looks like, how great operations leaders think like project managers, and product and sales lead grow. Art Harding on LinkedIn: https://linkedin.com/in/arhardingPeople.ai: https://people.aiEpisode Website: https://betweentwocoos.com/peopleai-coo-art-hardingMichael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Mar 17, 2022 • 49min
Uplight COO & fmr Symantec CSO, Angela Tucci on Reaching a $1.5B Valuation in 3 Years, Business as a Force for Good, B Corps, Reducing Carbon Emissions, Merging 6 Companies, and How Diversity Creates Safety
Angela Tucci, COO at Uplight, joins to talk about running a $1.5B company created from the M&A of 6 companies, advocating for voice & equity for women in the workforce, finding an inspiring CEO, working with utility companies to reduce their carbon footprint, taking private equity vs. VC funding, integrating acquisitions remotely during covid, the impact of politics, and systems thinking.Prior to Uplight, Angela was Chief Strategy Officer at Symantec, Chief Revenue Officer and Chief Marketing Officer at Rally Software, and Chief Executive Officer at Apto, so she's a clear underachiever. :)Uplight is a technology partner for energy providers and the clean energy ecosystem to help them reach their decarbonization goals. Uplight was last valued at $1.5 billion dollars, which is an achievement in and of itself, let alone for a company that's only 3 years old.Episode Website: https://betweentwocoos.com/uplight-coo-angela-tucci/Angela Tucci on LinkedIn: https://www.linkedin.com/in/angelatucci/Uplight: https://uplight.com/Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514 The 80/80 Marriage: https://www.8080marriage.com/

Mar 9, 2022 • 42min
Hotjar COO, Ken Weary on Remote-First with 220 Employees, Creating Remote Culture, Why Hybrid Work will Fail, Being a Digital Nomad Family, M&A and Doing Diligence on the Buyer
Ken Weary is the COO of Hotjar and joins to chat on running a fully remote 220 person company, being a digital nomad traveling for over 7 years as a COO with a family, going through M&A and diligence on the buyer, always having a just cause as the "why" behind what you do, the impact of remote on the great resignation, and bringing the Houses from Harry Potter to the workplace.Hotjar, is a European headquartered start-up with over 200 fully remote team members distributed across the globe. Ken is also a digital nomad and has been traveling with his family across Central America, Europe, and Africa for nearly 7 years.Prior to his travels, Ken held leadership positions in traditional corporate environments where he gained great experience but was tied to his desk. He relishes life “outside the cube”. Ken on LinkedIn: https://www.linkedin.com/in/kenweary/Hotjar: https://www.hotjar.com/Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Mar 3, 2022 • 36min
From the White House to a $20B IPO, Hiptrain COO & fmr Lyft Exec, Steve Taylor, on Managing a $500M P&L, the Why Behind the Pink Mustaches, Making the Analog Digital, Global Labor Arbitrage, & 3 Exits
Steve Taylor is an operating executive with experience building high-performing teams and scaling high-growth, category-defining companies. After spending the early part of his career flying E-2C Hawkeyes in the US Navy, he received a Masters of Policy Management from Georgetown University and spent five years as a management consultant. Steve joined Lyft in 2015 with just 220 employees, led two of the company's largest territories, launched multiple product lines, and managed a P&L with >$500M in annual revenue as we grew to 5,500 employees and a $20B IPO. In 2020, as COO at Fixt, with just 20 employees and $6M raised, he helped guide the company through a successful acquisition by Assurant (NYSE: AIZ), a $10B global insurance provider. He's now Co-founder and Chief Operating Officer at HipTrain, an online fitness company. Steve Taylor on LinkedIn: https://www.linkedin.com/in/stephen-h-taylor/HipTrain: https://hiptrain.comEpisode Webpage: https://betweentwocoos.com/hiptrain-coo-steve-taylor/Michael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514

Feb 23, 2022 • 34min
ExecThread CEO, Joe Meyer on Accessing Hidden Exec Retained Searches & How to Land Them, Exiting to Apple & AOL, Organic Supply/Demand Creation & Growth, the Motivation of Failure, & How to Overcome Any Challenge
Joe is Founder & CEO of ExecThread, a VC-backed crowdsourcing platform and premium job-sharing network that enables professionals to access the “hidden job market”. ExecThread is the largest global aggregator of unpublished executive-level job opportunities.Joe has been a successful start-up CEO and operating executive at high-growth tech companies including HopStop (acquired by Apple), Quigo (acquired by AOL) and eBay (EBAY) with a strong track record of recruiting teams, launching new products, raising venture capital, growing traffic, eliciting engagement, scaling revenue and achieving liquidity.Joe was named Entrepreneur of the Year in 2012 by Crain's New York Business, and was #9 on Business Insider's 2013 "Silicon Alley 100" list (as one of the Top 100 tech executives in NYC). Joe is a Board Member of the Hoyas Unlimited Board of Governors Company for Georgetown University, was previously on the Board of Directors of Kalexo (acquired by Autodesk) and Belief Networks (acquired by Benefit Focus), and also served on the Board of Advisors of Adtuitive (acquired by Etsy), Spongecell (acquired by Flashtalking, Inc., which was subsequently acquired by Mediaocean) and Snooth (wine discovery platform). ExecThread: https://execthread.comJoe Meyer: https://www.linkedin.com/in/joejmeyer/Michael Koenig: https://linkedin.com/in/mkoenig514/

Feb 15, 2022 • 47min
Kettle COO, & White House Innovation, Nathaniel Manning on Balancing Risk In A Changing Climate, Structure Without Bureaucracy, Evolution By Design, Good Decision Making, the Social Contract of Insurance, and Sitting on a Monastery Cushion for 3 Months
Kettle COO, Nathaniel Manning, talks about balancing risk in a changing climate, structure without bureaucracy, evolution by design, good decision making, the social contract of insurance, and sitting on a monastery cushion for 3 months. He also talks about old guard vs new guard, building the plane while it's flying, making the implicit explicit, and evolution by design.Nathaniel has a long career of founding and leading companies including Fellow Robots, BRCK, the largest provider of public wifi in Africa, and Ushahidi the world’s largest open-source platform for crisis response. Along the way, he worked on furthering clean energy as part of the Clinton Climate Initiative at the Clinton Foundation, and Nathaniel was part of the Obama Administration's first class of Presidential Innovation Fellow where he was special advisor on open data at USAID, the world's premier international development agency, where he went on to become the Chief Data Officer.With that kind of track record, it’s safe to say that Nathaniel puts his money where his mouth is when it comes to creating technological solutions to some of the world’s biggest problems. Nathaniel on LinkedIn: https://www.linkedin.com/in/nathanielmanning/Kettle: https://ourkettle.com/Episode Website: https://betweentwocoos.com/kettle-coo-nathaniel-manningMichael Koenig on LinkedIn: https://linkedin.com/in/mkoenig514