How the Deal was Done | Deal Stories Podcast

In this episode, Eric Hamilton, experienced sales leader shares insights on successfully closing a $900k total contract value transaction. And how to navigate a complex deal in the tech industry, emphasizing the importance of customer-centric strategies and teamwork. Background: The deal involved an automotive company, took six months to complete, involved multiple stakeholders from the buying and selling side, and was selling a cloud-based software solution. Challenges: Integrating the new solution within the client's legacy systems. Navigating the complex approval processes. Key Learnings: The significance of forging strong internal alliances and understanding the client's decision-making process. The necessity of being ‘persistently pleasant ‘and resilient during prolonged sales cycles. Timestamps: (00:05:12) Introduction and Eric’s career background and journey in sales (00:08:45) Overview of the deal (00:12:30) Challenges faced during the sales process (00:16:20) Navigating internal processes (00:20:55) Competition and Strategy (00:25:40) Key learnings from the deal (00:30:15) Final thoughts and advice for sellers Resources: LinkedIn: https://www.linkedin.com/in/erichamiltonblueprint/ Book: https://www.thesalesblueprintforsuccess.com/ Instagram: EricHamiltonSalesBlueprint Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

In this episode, Bion Behdin, Chief Revenue Officer of First AML, shares insights into winning a near million-dollar deal in the financial services and regulatory tech sector. Bion highlights the importance of strategic client engagement, internal stakeholder management, and leveraging feedback loops to navigate complex sales processes. Challenges: Securing buy-in amidst global company issues mentioned in the media. Managing internal stakeholder concerns and uncertainties about the deal's feasibility and execution. Key Learnings: Structuring deals with a detailed, proactive approach, including frequent summaries and clear next steps after discussions. Emphasize the importance of top company leaders staying close to client interactions and demos to understand customer needs and address potential challenges effectively. Timestamps: (0:01:44) Background and journey of Bion and First AML. (0:07:16) How the deal was initiated through a chance conversation at a pub. (0:10:24) Advancing through the RFP process and addressing technical requirements. (0:12:11) Importance of involving sales users and navigating internal stakeholder dynamics. (0:16:01) Overcoming challenges amid global company issues and internal concerns. (0:17:42) Learnings from structuring and negotiating large transactions effectively. Resources: LinkedIn: Bion Behdin Questions, comments, ideas - reach out to: Andrew Kappel

Shawn Curtis shares an intense negotiation involving a high-stakes deal at Spreedly, a payments orchestration company. He discusses overcoming internal challenges, strategic decision-making, and lessons learned from pivotal career transitions. Background: Shawn Curtis transitioned from a U.S. Navy career to sales, eventually becoming the first enterprise salesperson at Spreedly. The deal involved a major media conglomerate looking to expand internationally, challenging Spreedly's existing payments infrastructure; it took six months to complete with multiple team members involved in the negotiation. Challenges: Navigating a complex procurement process with stringent and unusual demands from the customer. Overcoming internal resistance and aligning multiple internal stakeholders to meet the deal's requirements and innovate on pricing models. Key learnings: The importance of aligning internal teams and stakeholders to support complex deals. The necessity of maintaining flexibility and openness in negotiations, adapting to unexpected demands and changes. Timestamps: (01:02) Meeting Shawn Curtis and the inception of a pivotal deal. (02:05) Entry into enterprise sales and initial challenges. (05:12) Crucial negotiations and internal alignments. (10:48) Strategic pivot and high-level negotiations with the media conglomerate. (16:04) Critical email and breakthrough in the deal process. (18:29) Finalizing the deal and reflecting on the arduous process. (23:18) Shawn Curtis’s insights on enterprise sales strategies and career growth. Resources: Shawn's LinkedIn RepVue | Sales Organization Ratings, Reviews, Jobs (where Shawn is the Director of Sales) Questions, comments, ideas - reach out to Andrew Kappel

Colin Specter shares his experiencing becoming the top seller at his company and a formative deal that he fell short on and what he learned from it. Background: Colin Specter started his career in SaaS sales at Namely where he became a top 1% seller and progressed to a leadership role now at Orum. The deal involved namely, a tech company specializing in HR software, to the CFO of a large financial services company Challenges: Failing to better understand a company’s broader culture and norms. Facing to check overconfidence when a deal seems to be made already Key learnings: Research and adapt to the corporate culture and expectations of potential clients, especially regarding dress codes. Building a strong relationship with various stakeholders, not just the primary contact, to navigate corporate dynamics effectively. Timestamps: (0:10:25) Immediate Judgment Based on Attire... Colin describes the moment his attire led to a snap judgment by the CFO. (0:13:09) Cultural Missteps and Adaptations... Colin discusses adapting to different corporate cultures. (0:13:56) East Coast vs West Coast Business Culture Differences... Insights into differing business practices between "New York" and "California" businesses and startups. (0:16:47) Building Partnerships and Networks... The importance of building networks and how past connections influence current opportunities. (0:19:23) Learning from Losses... Reflecting on how losses can be more memorable and educational than wins. Resources: Colin's LinkedIn The Nazare Wave  Episode with Ewing Gillaspy Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/Podcast Questions, comments, ideas - reach out to Andrew Kappel

John Barrows, one of the top sales trainers and thought leaders, joins for a look back on his journey and fun discussion on a particularly large and memorable deal from his time at Thrive Networks. Background: John Barrows has 20+ years of sales experience with a variety of companies and as an entrepreneur In this episode he remembers a managed IT services deal he did that was 20x the avg. deal size Challenges: Establishing trust and staying top of mind without being perceived as annoying. Adapting to the evolving sales landscape and shifting from traditional tactics to leveraging technology effectively. Key learnings: The value of playing the long game in sales and building meaningful relationships over time. The necessity of adapting to changing sales environments and leveraging technology to stay competitive. Timestamps: (0:07:28) Reflecting on the challenges faced at a big company versus startups and working on your own (0:13:16) Sharing a specific deal that highlighted the value of persistence and relationship-building. (0:17:14) Utilizing low-tech tactics and the significance of fundamentals in sales. (0:21:20) Discussing the relevance of agility and adaptation in the fast-evolving sales landscape. (0:24:37) Exploring the concept of the infinite game and the importance of aligning with personal values in sales. Resources:John Barrows on LinkedIn The Infinite Game: Sinek, Simon John’s Newsletter John's Podcast Questions, comments, ideas - reach out to: Andrew Kappel

Amanda Brem, founder of the Brem Method, recounts how she pitched and executed her first academic coaching course for pre-medical students, overcoming skepticism and challenges along the way. Through determination and leveraging her strengths, she successfully built a thriving business despite initial uncertainties. Background: Amanda Brem founded the Brem Method, specializing in academic coaching for pre-medical students She secured a deal with a program director to run an academic course for MCAT preparation Challenges: Convincing the program director to take a risk on an unproven product, addressing concerns about potential negative feedback impacting future enrollments. Navigating the complexities of contract negotiations as a small company, especially in contrast to dealing with larger institutions. Key Learnings: Embracing negative feedback as critical feedback to improve and not fearing it as a threat to reputation. Understanding the importance of commitment and follow-through in sales, avoiding second-guessing decisions to ensure success. Timestamps: (0:00) Introduction and background of Amanda Brem and the Brem Method. (5:36) Amanda's experience in sales during her time as a personal trainer and the importance of developing a niche. (7:58) Initiating the deal with the program director and challenges faced during the process. (11:30) Scaling the business and expanding beyond the initial pilot program. (13:18) Sources of information and learning for sales and entrepreneurship. (17:24) Challenges and anxious moments faced during the pitch and contract negotiations. (19:40) Moments of uncertainty and key learning points throughout the deal process. Resources: LinkedIn: [Amanda Brem - Founder - The Brem Method](https://www.linkedin.com/in/amandabrem) YouTube: https://www.youtube.com/channel/UCCs_enSv2UntPXD33e6b6Dg Questions, comments, ideas - reach out to the host: https://www.linkedin.com/in/andrewkappel/

Drew Wills shares his journey from a senior in college struggling to find a job to impressive runs at LinkedIn and Gong and now becoming VP of Sales at Brilliant. Drew emphasizes the importance of networking, leveraging LinkedIn, and sales negotiations. The podcast highlights Drew's approach to renewing a significant deal with a customer by demonstrating indispensable value and learning from past negotiation experiences. Background: •    Drew Wills transitioned from numerous roles at LinkedIn to a leadership position at Gong and now VP of Sales position at Brilliant. The deal, aiming for renewal with a focus on demonstrating value to resist competitive threats. Challenges: •    The rise of the CFO's role in procurement made negotiations tougher, requiring more than just the demonstration of the product's value. •    The shift from growth at all costs to profitability among companies put additional pressure on software services to justify their costs amid layoffs and budget cuts. Key Learnings: •    The importance of building a strong case with the users of the product to ensure internal advocacy during renewal negotiations. •    Clarity on dates and deadlines can significantly impact the negotiation outcome by preventing the extension of discussions beyond the expiration date. Timestamps: •    (0:01:30) Drew Wills intro and career background. •    (0:03:29) Experience and roles at LinkedIn. •    (0:07:51) Discussion on the deal at Gong and the shift in the procurement landscape. •    (0:11:29) Strategies for maintaining price points and demonstrating value. •    (0:17:24) Negotiation tactics and learning from past deals. •    (0:22:38) Drew's new role at Brilliant and the value of corporate gifting. •    (0:25:34) Approaches to sales and business development at Brilliant.Resources: Resources: LinkedIn: https://www.linkedin.com/in/drewwills/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast (http://orgcharthub.com/podcast) Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/ (https://www.linkedin.com/in/andrewkappel/)

Ep. #33 featuring entrepreneur Tom Cates who has a decades long career as a consultant, sales leader, and software founder. Tom got his start in sales with IBM, an MBA from Wharton, moving into management consulting, and eventually starting his own consulting firm and software company focused on B2B business relationships. Background: Tom shares insights on selling high-value B2B products and services and the importance of establishing meaningful, differentiated relationships with clients. The deal story involved a multibillion-dollar IT services client, with the engagement starting around 2017/2018 on a three-year agreement basis, involving a software product aimed at improving client relationships beyond conventional metrics like Net Promoter Scores. Challenges: Showing the client that their success metrics (like Net Promoter Scores) were inaccurate signs of growth and they needed to find new ones. Demonstrating the unique value of their software and consulting services as an unknown entity to a major outsourcer. Key learnings: Getting more customers to promote your product/service revolves around the experience of the "middle" customers (those somewhat satisfied but not fully engaged) rather than focusing solely on detractors or promoters. Success depends not just on delivering value, but also on effectively communicating this value to the right people within the client organization. Timestamps: (0:00:36) Tom Cates intro and background (0:02:06) Acton, Massachusetts where Tom Cates and Andrew Kappel (host) are from (0:04:33) Discussing the lifetime value of a customer (0:06:25) Finding and following your passion (0:09:27) Unpacking the disconnect between high NPS scores and growth (0:15:43) The Christmas tree analogy in sales Resources: LinkedIn: https://www.linkedin.com/in/tomcates/ Tom’s consulting firm: http://www.encompass-cx.com/ Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Donald Kelly, highlights the challenges and strategies involved in closing a large-scale deal with a school district. Kelly shares insights on the importance of acting as a consultant rather than an order taker and the lessons learned from navigating a complex sales process. Background: Donald Kelly transitioned from various sales roles into the founder of a sales training firm and podcast host. The deal discussed was with a school district, involving document management solutions, taking two years to close, and was valued at approximately $150,000. Challenges: Gaining access to key decision-makers and influencers beyond the purchasing director, and navigating a lengthy and specific buying cycle within the school district. Initially lacking a comprehensive understanding of the client's deep-rooted problems and the need to custom tailor solutions beyond standard offerings. Key learnings: The importance of establishing relationships with key stakeholders and understanding their personal and professional motivations for the deal. Adopting a consultant mindset, focusing on value and impact rather than price, and the necessity of thorough preparation and adaptability in sales strategies. Timestamps: The Sales Evangelist Journey (0:01:41-0:03:41) Overcoming Podcasting Challenges (0:03:41-0:06:19) Navigating a Complex School District Sale (0:06:19-0:11:22) Strategic Planning and Board Approval (0:16:45-0:19:29) Lessons Learned and Wrap-up (0:19:29-0:26:50) Connect with Donald on LinkedIn: https://www.linkedin.com/in/donaldckelly/ Listen to Donald's Podcast here: The Sales Evangelist Donald KellyApplehttps://podcasts.apple.com › podcast › the-sales-evangelist Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/

Jake Dunlap, CEO and Founder of Skaled Consulting, has worked on thousands of deals, and now he shares his expertise with organizations looking to accelerate their growth. In this episode he recounts a three part deal that grew to $4M in ten months and the sales strategies and philosophies to get there. Background: Jake Dunlap is CEO Skaled Consulting. Has worked on thousands of deals and shares one from earlier in his career that shaped future strategies Key Challenges: Adapting to client budget cycles. Overcoming traditional contract limitations. Navigating enterprise decision-making timelines. Key Learnings: Importance of aligning with client budgets. Using "proof of concept" and "proof of scale" for deal expansion. Flexibility in contracts secures larger partnerships. Timestamps: (1:28) Discussion on Strategic Sales Contracts and Aligning with Client Budget Cycles (6:05) Challenges in Adapting Sales Strategy to Enterprise Decision-making (10:06) Insights on Utilizing "Proof of Concept" to "Proof of Scale" for Deal Expansion (15:04) Jake's Learnings on Flexibility and Customer-Centric Contracts (19:30) Conclusion and Key Takeaways Order Jake's new book at: https://www.jakedunlap.com/the-innovative-seller Find Jake on LinkedIn:  https://www.linkedin.com/in/jakedunlap/ Join the Innovative Seller Community Summit: https://www.jakedunlap.com/the-innovative-seller-community-summit Custom GPTs for Sales: https://skaled.com/insights/custom-gpts-for-sales/ Workshop + Prompt Pro: https://bit.ly/accelerator-and-prompt-pro Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast Questions, comments, ideas - reach out to: https://www.linkedin.com/in/andrewkappel/