

How the Deal was Done | Deal Stories Podcast
Andrew Kappel
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/
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/
Episodes
Mentioned books

Jan 3, 2024 • 30min
Ep. 20: Closing a Multi-Million Dollar Deal with 100 Stakeholders with Global AE Matthew Klingner
Timestamps
- (0:00:29) Matthew Klingner Intro.
- (0:03:46) Matthew’s career transition and sales philosophy.
- (0:06:39) Differences between transactional and enterprise selling.
- (0:11:30) Overview of the multimillion-dollar deal.
- (0:17:51) Managing over 100 stakeholders and internal challenges.
- (0:20:04) Importance of internal and external champions in closing the deal.
- (0:25:18) Matthew’s approach to personal and professional growth.
Connect with Matt on LinkedIn: https://www.linkedin.com/in/matthewklingner/
Check out his sales course and coaching here: https://matthewklingner.gumroad.com/l/7FigureSelling
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 - connect with host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/

Dec 27, 2023 • 39min
Ep. 19: How the Deal Was Done Holiday Special Behind the Scenes
In this episode, Andrew welcomes How the Deal Was Done sponsor, Dan Currin, Co-Founder of OrgChartHub, to discuss how the deal to make this podcast was done and reflect on the journey thus far. Andrew also introduces the people behind the scenes, Brett Muni (Producer) and Bilal (Video and Content Partner), who've helped get this show off the ground and running.
Connect on LinkedIn with our sponsor Dan Currin Co-Founder OrgChartHub: https://www.linkedin.com/in/danieljcurrin/
Connect with our Podcast Producer Brett: https://www.linkedin.com/in/brettmuni/
Connect with our Video Content partner Bilal: https://www.linkedin.com/in/iambillal/
Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub has been helping HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast
Learn more about Bilal's content services at https://iambillal.com/ as well.
And link to Editor/Producer Brett’s White Lotus remake trailer ep from his travels in Italy:
https://www.instagram.com/reel/CregQb4Joff/?igsh=MzRlODBiNWFlZA==

Dec 18, 2023 • 14min
Ep.18: Harnessing Board Members to Advance and Close Enterprise Sales with Jeff Kirchick
Jeff Kirchick, shares his journey and insights on a complex deal between his fintech SaaS co. and a bank. The deal involved complex buying group and multiple challenges with a startup selling into financial services. Resistance to change can be the name of the game.
Jeff shares tips to level up engagement and how-to for getting Boardmember and President-level stakeholders involved. If you are interested in hearing how senior-level stakeholders can be utilized strategically to get deals unstuck and converted, check out this episode!
Connect with Jeff on LinkedIn: https://www.linkedin.com/in/jeffkirchick/
Check out his award winning book: https://www.amazon.com/Authentic-Selling-Principles-Sales-Everyday/dp/1735956902
Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done. Learn more at OrgChartHub.com/podcast
Questions, comments, ideas - reach out to:
https://www.linkedin.com/in/andrewkappel/

Dec 11, 2023 • 39min
Ep.17: 8-Figure Transformation Deal with former Salesforce #1 Rep Ian Koniak
Big Deal Story Alert. Ian, a former #1 enterprise account executive at Salesforce shares his journey from transactional to enterprise selling. He detailed his 8 figure deal with Berkshire Hathaway Home Services, where he faced initial rejection and then re-grouped and re-positioned to land one of the largest deals in Salesforce history. Great story for sellers and leaders to think big for 2024!
# Timestamps:
[0:01:11] - Background: Ian shares his journey from transactional to enterprise selling.
[0:03:25] - Deal Setup: Intro to Account Current State and explaining scale and context of the company (50,000 real estate agents).
[0:07:10] - First Challenges: Details on initial challenges and rethinking strategy based on initial rejection in the account.
[0:11:43] - Uncovering Larger Needs: identifying broader challenges within client’s organization, going beyond the initial project scope.
[0:12:08] - Diving Deep into Client’s Problems: Further exploration of the client's internal struggles and market challenges.
[0:19:11] - Selling the Vision: how to sell the change vision.
[0:21:02] - Gaining Momentum: gaining traction by aligning with the client's top priorities and business needs.
[0:23:18] - Outmaneuvering Competition & Closing the Deal: how Ian positioned Salesforce uniquely, reducing competition.
[0:34:03] - Advice for Transitioning Sellers: Ian's advice for transactional sellers looking to move into enterprise selling.
Connect with Ian on LinkedIn: https://www.linkedin.com/in/iankoniak/
Resources from Ian:
Free Enterprise Sales Training:
HOW TO MAKE $500,000 TO $1,000,000/YEAR IN TECH SALES
Learn more about Ian's Coaching Programs & Community:
https://www.untapyoursalespotential.com/
Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at http://orgcharthub.com/podcast
Questions, comments, ideas - reach out to:
https://www.linkedin.com/in/andrewkappel/

Dec 4, 2023 • 14min
Ep 16. Selling to the Fortune 500 as an Early Stage Startup featuring Joe Benjamin
# TIMESTAMP
1. (0:00:53) - Joe's background as early stage sales expert and multi-time founder.
2. (0:03:26) - How this deal got started through hosted event(s)
3. (0:05:39) - Top-down sales cycle and building trust.
4. (0:09:15) - Joe's insights on running similar plays for early stage startups
Connect with Joe on LinkedIn and learn about his company RevPilots: https://www.linkedin.com/in/joebenjamin1/
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 for the podcast? Reach out to Andrew Kappel on LinkedIn
https://www.linkedin.com/in/andrewkappel/

Nov 27, 2023 • 13min
Ep 15. Enterprise Deal to Pre-IPO Grocery Delivery Start-Up with Ben Richardson
In this episode of Ben Richardson shares his experience working on a big deal with an innovative pre-IPO grocery delivery company. He highlights the challenges of integrating financial systems post-acquisition and the role of his solution in automating financial and billing processes to support the company’s rapid growth.
What you will learn?
The episode offers valuable insights into strategic partnerships, competitive positioning against rivals, and the importance of executive alignment and stakeholder management in closing enterprise deals.
**Timestamps:**
- (0:04:50) - Overview of the grocery delivery company’s situation and its needs as it prepared for IPO.
- (0:05:23) - The role of a key partner in initiating the deal and the early stages of discovery and engagement.
- (0:06:28) - Insights into the competitive landscape and leveraging customer references.
- (0:09:22) - Discussion on the importance of aligning with executives and stakeholders for deal success.
- (0:10:04) - Ben reflects on personal growth areas, particularly in negotiation, and key learnings from the deal.
Connect with Ben on LinkedIn: https://www.linkedin.com/in/benrichardsonsf/
Book Mentioned: Bargaining for Advantage on Amazon: https://www.amazon.com/Bargaining-Advantage-Negotiation-Strategies-Reasonable/dp/0143036971
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 about the Show - reach out to Andrew Kappel at https://www.linkedin.com/in/andrewkappel/

Nov 20, 2023 • 18min
Ep 14. Understanding Customers to Create & Close | How the Deal and Partnership Was Done with Sean Adams
In this episode we meet Sean Adams: the head of Sales and Partnerships at Iorad. Sean brings a wealth of experience to the table. He started his career as a business owner, serving home service businesses in the contractor space for a decade. Then, he entered the world of SaaS as an account executive and now leads sales operations with a focus on customer centricity.
Thinking Outside the Box: Sean shares a challenging situation from a past company where deals were constantly stalling due to issues with customers' accounting systems. Sean worked to establish a connection between the systems. This innovative solution allowed the technology to seamlessly communicate with each other, eliminating the barriers that were holding back deals. The outcome was transformative – deals started to flow smoothly, and lost opportunities became closed deals.
Overcoming Obstacles and Gaining Insight: During his strategic partnership and deal journey, Sean faced internal management obstacles. He engaged in no-obligation interviews with prospects and customers. However, as Sean and his team began to better understand customer issues with accounting software such as QuickBooks, and used video footage of them explaining their issues to persuade internal stakeholders.
Instilling Creativity and Tenacity: As the head of sales and partnerships, Sean Adams shares his approach to instilling creativity and tenacity among his team. Rather than just telling his team what to do, he leads by example and brings new talent into calls and meetings to watch and learn how it is done.
TIMESTAMPs
(0:00:29) - Sean Adams is the head of Sales and partnerships at Iorad
(0:02:58) - Software company had problems with material syncing between accounting system and supplier
(0:06:14) - You've connected the dots between SaaS and technology
(0:07:50) - So talk about some of the obstacles or where some of your master plan went off the rails
(0:11:40) - We'd love to hear about the outcome and then some of the learnings since then
(0:13:56) - Sean is the head of sales and partners at Iorad
(0:16:47) - Sean, this has been really insightful and can we point folks or where should we point
Connect with Sean on LinkedIn: https://www.linkedin.com/in/sean-adams-sales/
Check out Sean's Best Practice Article for those interested in being a guest on a podcast: https://www.linkedin.com/pulse/how-become-guest-your-dream-podcasts-sean-adams/
Questions, comments, tips - reach out and connect with Andrew on LinkedIn https://www.linkedin.com/in/andrewkappel/

Nov 13, 2023 • 16min
Ep.13: $8 Million Competitive Takeout Deal with Danny Brown
Episode with Danny Brown, a seasoned entrepreneur and CEO of AppMeetup. Danny shares valuable insights into a pivotal deal from his early business experience.
What you will learn?
Building trust as an unknown entity, speaking the client's industry-specific language, and overcoming the resistance associated with replacing a familiar product.
# TIMESTAMP
- (0:02:07) - How to differentiate when the customer is trying to commoditize your product or service
- (0:04:55) - The importance of maximizing the use of tools like Gong for sales insights.
- (0:06:18) - The potential for AI tools to enhance sales efforts.
- (0:08:17) - Challenges faced in the early stages of a business.
- (0:10:43) - How to approach client-centric strategy.
- (0:13:03) - Approach for personal growth through reading, podcasts, and audiobooks.
- (0:14:51) - Danny provides information about where to find more about his training programs, books, and podcast.
Danny's Book: Talk it Up!: A Guide to Successful Public Speaking
Connect with Danny on LinkedIn: https://www.linkedin.com/in/dannysbrown/
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 about the Show - reach out to Andrew Kappel at https://www.linkedin.com/in/andrewkappel/

Nov 9, 2023 • 18min
Ep.12: From selling a partnership to selling the whole company to HubSpot | How the Deal was Done with Mawghan McCabe
In this episode, we hear from Mawghan McCabe, Director Platform Partnerships at HubSpot. Mawghan shares her unique journey from her sales background in New York to working with Piesync in Belgium, eventually becoming part of the HubSpot team.
She discusses the intricacies of the Piesync HubSpot deal, which initially started as a funding discussion but later transitioned into a complete acquisition. One of the pivotal factors in this shift was Piesync's customer-centric approach. Their focus on building strong customer relationships and their proactive engagement with clients became a compelling reason for HubSpot to opt for an acquisition.
Mawghan emphasizes the importance of adaptability in negotiations, advocating for a mindset open to unexpected outcomes.
Keys: being customer-centric, fostering meaningful partnerships, and remaining agile in the ever-changing landscape of business deals.
Timestamp:
(0:01:47) - Mawghan's background and story of going from Director of Sales at a US company and then relocating to Europe
(0:08:40) - Tips for Attracting customers and partners as a small startup
(0:14:17) - Why getting your foot in the door is the most important thing
(0:16:06) - Wrap up and best practices for learning & development
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Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast
Connect: on LinkedIn Mawghan (Morgan) McCabe
https://www.linkedin.com/in/mawghan/
Questions, Comments, Ideas about the Show - reach out to Andrew Kappel at https://www.linkedin.com/in/andrewkappel/

Oct 30, 2023 • 13min
Ep.11: Taking an Additive Approach to Partnership Sales with Barrett King former HubSpot Sr. Manager Global GTM Strategy
Barrett King, a partnership expert and Sr. Director, Revenue at New Breed joins to share an interesting deal story from his time as a Channel Partner Manager at HubSpot.
Barrett re-engages with the CEO of a digital agency who had previously declined to partner with HubSpot.
Best Practice: taking an additive, not transformative approach to connect with prospects and highlight what a successful technology (HubSpot) and services (digital agency) partnership can look like.
Take a listen to hear best practices on indirect sales and partner motions. Designing Win-Win solutions, and why partnerships will be key this next decade.
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Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast
On Taking Action from Advice:
How high are you flying? What's your perspective right now? The way to action on advice is to be very intentional around the lens that we take the perspective that we approach it from. It's ultimately about how high you are flying. Are you in the weeds at 500ft being very tactical actionable and you can only see 100ft down the road in front of you, or is your head picked up? Are you flying at 30,000ft and you're looking at the higher landscape? Or perhaps you're somewhere in between and it gives you a little bit of tactical, but also perspective. I think that's the best way.
Quote:
"We're going to see more and more companies implement this partnership methodology because one plus one is three, and you build a value triangle around that. The customer wins, and therefore you and your partner win as well. It's a no brainer."
Connect: Find Barrett on LinkedIn and ask him about "3 in 30"
https://www.linkedin.com/in/barrettjking/
Questions, Comments, Ideas about the Show - reach out to Andrew Kappel at https://www.linkedin.com/in/andrewkappel/