How the Deal was Done | Enterprise Sales Podcast

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/

In this episode Andrew shares a solo deal story from his consultancy: Benchmark Signal Consulting. Other topics mentioned- podcast growth initiatives including the new YouTube channel and some big upcoming guests. Resources mentioned: https://perell.com/essay/imitate-then-innovate/ Episodes Referenced: https://www.dealstoriespodcast.com/episodes/ep-21-special-edition-buyer-se YouTube: https://www.youtube.com/@HowtheDealWasDone 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/

Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the buying company’s share price. This deal is a perfect example of the power of internal champions and genuine customer relationships. Background on Jesse and the deal: Jesse Woodbury is a seasoned sales professional and Sales Players podcast host The lead came inbound from a UX manager who was reaching out to several vendors Deal Challenges: Initial lack of a clear pain point or urgency from the client's side, making it difficult to push for a substantial commitment. Distinguishing their company from the many other vendors in consideration Navigating the complexities of negotiating an unlimited usage pricing model which Jesse’s company did not regularly offer Key Learnings: The importance of building genuine relationships and having an internal champion within the client's organization can significantly influence the deal's outcome. Creative deal structuring and flexibility in pricing can open doors to larger opportunities and partnerships. Persistence and the ability to adapt sales strategies to meet client needs and internal changes can lead to groundbreaking deals. Timestamps: 0:02:24 - Jesse shares his encounter with Tim Ferriss, showcasing his admiration and the unexpected meeting that influenced him. 0:03:43 - Jesse mentions how Dustin Brown, a mentor and friend, has influenced his approach to enterprise selling. 0:08:45 - The background of the deal Jesse is discussing begins, detailing the initial contact with the UX manager from a large B2C Home Services Company. 0:15:39 - Discussion on the transition of the deal from a small proof of concept to a major project with executive involvement, including strategic outreach and negotiation phases. 0:27:21 - Jesse reflects on the impact of the deal, not just on his career but also on the client's business, highlighting the mutual benefits and the importance of relationship-building in sales. 0:29:35 - Closing remarks from Jesse and Speaker C, with an invitation for listeners to connect and explore further content. LinkedIn: https://www.linkedin.com/in/jessewoodbury/ ‘Sales Players’ podcast: https://open.spotify.com/show/1n4giaqOn4KvM9dk8b6Nm2 Jesse referred by Dustin Brown - link to Dustin Brown episode: https://www.dealstoriespodcast.com/episodes/ep-25-expanding-a-fortune-50-a 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/

Max Tipton, VP of Sales North America for Paperless Parts, shares the story behind a transformative deal known as "The Earth Mover". Background: A pivotal deal known as "The Earth Mover." The deal was with a major custom part manufacturer in the U.S., aiming to revolutionize their estimation and quoting process. This opportunity was significant for Paperless Parts, marking a strategic push into larger market segments. Challenges: High-Level Engagement: Starting the conversation at the CEO level set high expectations for alignment and delivery. Defining Success Criteria: The client's initial lack of detailed success and technical requirements posed significant hurdles. Build vs. Buy Decision: Convincing the client to choose Paperless Parts' solution over developing an in-house solution. Key Learnings: Executive Bridge Building: Early executive engagement between both companies' CEOs proved critical for trust and alignment. Collaborative Requirement Definition: Working closely with the client to detail their success criteria and technical needs was key. Strategic Patience: The deal required a balanced approach of maintaining momentum while allowing the client time for internal decision-making. Timestamps: 0:00:00 - Introduction and early strategies in deal-making 0:01:27 - Max's journey in sales 0:04:23 - Background on the transformative deal 0:08:09 - Challenges encountered during the deal 0:10:34 - Key strategies used in the deal 0:13:03 - Closing strategies and the role of executive relationships 0:16:23 - Learnings from the deal and its impact on future sales Connect with Max and learn more about Paperless Parts on LinkedIn: https://www.linkedin.com/in/maxtipton/ 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/

In this special episode host Andrew Kappel, and producer Brett Muni reflect on some of the most popular episodes so far, explore how these lessons have impacted Andrew's Sales Consulting Business, and enlist the audience to connect with us on LinkedIn to let us know what content has been the most engaging. Timestamps: 0:01:54 - Discussion on the podcast journey and the milestone of 25 episodes 0:04:29 - Insights on enterprise sales, project management, and the impact of big deals 0:10:30 - Introduction to Benchmark Signal Consulting and the Gong audit and optimization offering 0:12:22 - A look into consulting deals and the project 5000 initiative 0:17:33 - The importance of multi-threading and building a strategic sales pipeline 0:19:12 - Closing remarks and invitation for feedback Connect with Andrew Kappel: https://www.linkedin.com/in/andrewkappel/ Connect with Brett: https://www.linkedin.com/in/brettmuni/ Skip Miller with more train analogies: https://www.linkedin.com/posts/skip-miller-a7243_really-its-about-the-trains-here-i-am-activity-6327423369071464448-dfrQ/?originalSubdomain=uk Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at ⁠OrgChartHub.com/podcast