40 episodes

How the Deal was Done | Deal Stories Podcast features fast-paced interviews with top sellers & leaders.

Insights and Inspiration.
1. You will hear the story for how a large deal was won 2. We'll cover the backstory, challenges, and learnings picked up along the way. All in about 15 minutes.

If you have questions or would like to recommend a guest please connect with Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/

How the Deal was Done | Deal Stories Podcast Andrew Kappel

    • Business
    • 4.6 • 7 Ratings

How the Deal was Done | Deal Stories Podcast features fast-paced interviews with top sellers & leaders.

Insights and Inspiration.
1. You will hear the story for how a large deal was won 2. We'll cover the backstory, challenges, and learnings picked up along the way. All in about 15 minutes.

If you have questions or would like to recommend a guest please connect with Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/

    Ep. 40: Exec Alignment, Surprise Onsites, and End of Quarter Plays to get the Deal featuring Eric Hamilton

    Ep. 40: Exec Alignment, Surprise Onsites, and End of Quarter Plays to get the Deal featuring Eric Hamilton

    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/

    • 26 min
    Ep 39: Complex International Financial Services Deal with Bion Behdin, Co-Founder and CRO First AML

    Ep 39: Complex International Financial Services Deal with Bion Behdin, Co-Founder and CRO First AML

    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

    • 22 min
    Ep. 38: Rep Boomerang 7-figure Transformation Deal featuring Shawn Curtis

    Ep. 38: Rep Boomerang 7-figure Transformation Deal featuring Shawn Curtis

    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

    • 28 min
    Ep. 37: How the Deal Was *Not* Done, Navigating Cultural Differences with Colin Specter

    Ep. 37: How the Deal Was *Not* Done, Navigating Cultural Differences with Colin Specter

    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

    • 20 min
    Ep. 36: Playing the Long Game to Win Deals, Stay Agile, and Keep Going featuring John Barrows

    Ep. 36: Playing the Long Game to Win Deals, Stay Agile, and Keep Going featuring John Barrows

    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

    • 30 min
    Ep.35: Selling the Vision Before Building the Product featuring Amanda Brem, Founder - The Brem Method

    Ep.35: Selling the Vision Before Building the Product featuring Amanda Brem, Founder - The Brem Method

    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/

    • 22 min

Customer Reviews

4.6 out of 5
7 Ratings

7 Ratings

Andrew_Kappel ,

Insights and inspiration

Fast-paced, actionable deal stories. Solid for those in complex enterprise sales. The IBM buyer-seller episode was a great one. I think ep 21.

LinkedIn guy ,

Solid for SaaS

Love the cautionary tales and easy to retain lessons

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