

How the Deal was Done | Enterprise Sales Podcast
Matthew Klingner | Andrew Kappel
How the Deal was Done: Fast-paced interviews with top sellers & leaders.
Each week we sit down with the best enterprise sales executives and Founders to unpack transformational deals & discuss the mindsets, strategies, and actions of world class performers.
Each week we sit down with the best enterprise sales executives and Founders to unpack transformational deals & discuss the mindsets, strategies, and actions of world class performers.
Episodes
Mentioned books

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/

Oct 23, 2023 • 14min
Ep.10: Standing Up a HealthTech Startup from Day 0 to a $1M Account | How the Deal was Done with Jerry Barsz
This episode features Jerry Barsz, a top seller and leader currently working for a health tech startup.
Jerry joined Optimize Health as the first commercial hire. He has gone on to become a sales leader and now heads up strategic partnerships as the company continues to grow. Jerry shares learnings from being a part of a major product and company pivot. And how winning a major deal in the early days accelerated growth in revenue, technology, and processes.
Tune in to hear the skillset and mindset needed to be successful in startup sales and leadership.
Connect with Jerry on LinkedIn: https://www.linkedin.com/in/jerryabarsz/
Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast

Oct 16, 2023 • 16min
7-Figure Competitive Displacement | How the Deal was Done with Kishan Patel
In this episode, we welcome Kishan Patel, who shares a deal story of 7-figure pilot that goes onto become a multi-million dollar transformation deal for a large health insurer.
Background:
- Kishan Patel has over 11 years of experience in the enterprise space, with a focus on payments and ecommerce risk management.
- Solution is data and IT infrastructure solutions for a large Fortune 500 Health Insurer.
Challenges:
- Displacing the top vendor.
- Complex pilot.
- Stakeholders from various teams and functions with varying objectives (11 stakeholders, 70+ conversations)
Learnings:
- importance of having an executive sponsor or coach to navigate the challenges and filter out the noise.
- The use of video production in a stakeholder presentation to stand out and quickly get all stakeholders on the same page
– understanding the client's perspective and aligning the narrative with their goals.
Connect with Kishan on LinkedIn:
https://www.linkedin.com/in/1kpat/
Thank you to OrgChartHub for Sponsoring this episode. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast
Timestamps:
:29 - Seller Background Kishan Patel Background
2:08 Deal Background: million dollar pilot for a large health insurer
05:39 - Challenges. Blockers everywhere you went. Oftentimes it was access to that information
06:45 - Buying Group Dynamics
08:48 - Creating a Video Production with Customers to explain the value narrative in the stakeholder meeting
11:38 - Biggest learnings and takeaways

Oct 9, 2023 • 14min
Selling With Your Buyer | How a B2B Deal with Facebook gave Nate Nasralla the idea to launch Fluint.io
Nate Nasralla, sales leader, author, and co-founder of Fluint.io share a unique and fascinating story of a deal he sold to Facebook. And how that deal helped give him the idea to build his new Buyer Enablement app: Fluint.
Background:
Selling into Fortune 500 Digital Innovation Team
Global Stakeholders and Custom Needs
Only access to one contact
Key Actions:
The importance of enabling buyers' champions to effectively sell internally.
The value of transforming sales conversations into written cases
The value of interacting with the buying committee in a buyer-centric way
Learnings:
How to earn the trust of your champion
How to make it easy for your champion to sell internally
And how to understand how solid or not your deal is - without meeting the Exec Sponsor
This episode is sponsored by OrgChartHub. OrgChartHub helps HubSpot customers get big deals done since 2018. Learn more at OrgChartHub.com/podcast
Pre-Order Nate Nasralla's new book (releasing Nov 9. 2023): Selling With: The art of selling with champions to shape internal buying conversations & close enterprise deals
Learn more about Nate and Fluint.io at https://www.fluint.io/blog

Oct 2, 2023 • 16min
Ep.7: Learnings from selling 700+ customers as an Account Exec at ZoomInfo with Dustin Phillips
Dustin's background and 8+ year journey at ZoomInfo (1:15)
Dustin's specialty niche for professional sports team; outbound sourced 50+ deals (2:30)
Overcoming challenges including objections and timing issues that prevent deals from getting done (8:50)
Learnings from selling over 700 customers as an Account Exec at ZoomInfo (10:18)
Listen for the full detail on How the Deal was Done.
Sponsor: OrgChartHub has been helping HubSpot CRM Customers get big deals done since 2018. Visualize your accounts, see key stakeholder roles, and understand relationships at a glance. Check them out at www.OrgChartHub.com/podcast


