

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

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

Sep 25, 2023 • 14min
Ep.6: Using a Greek Mythology Book to creatively Prospect and Close a 7-Figure Deal with Tom Alaimo
In this action-packed episode, Tom Alaimo takes us through a captivating and exciting deal story in which he got in the door by sending an obscure Greek mythology book to the CEO of a major tech company. This got him referred to the CMO where he played the long game and built a relationship. That is just the start. Listen to the whole episode to hear the ups and downs and how the deal ultimately got done!
Sponsor: OrgChartHub
Visualize your accounts, see key stakeholder roles, and understand relationships at a glance.
OrgChartHub has been helping HubSpot CRM Customers get big deals done since 2018.
Check them out at www.OrgChartHub.com/podcast
Show Notes
- Tom Intro and Background - Never Missed a Presidents Club!
- How the Deal Started
- Challenges including Director and VP-level blockers
- Getting the Deal Closed and Key Learnings
- What makes Tom unique as a seller
Links & Resources
Tom’s Podcast: Millennial Sales | Podcast on Spotify
Link to Connect on LinkedIn: Tom Alaimo (be sure to check out his 7-Figure Prospecting Boot Camp and Arise Immersion Events)

Sep 12, 2023 • 23min
Ep.5: How the Deal was Done | Selling a $34 Million SaaS Deal with Evan Kelsay
In this episode, Evan Kelsay takes us through the fascinating journey of closing a $34 million SaaS deal. He shares how this deal began with a small customer engagement and evolved into a transformative partnership with his small (300 person startup - Seismic) selling a deal to one of the largest companies in the world.
Evan shares a mini-masterclass on researching and identifying potential opportunities, going outbound to get the ball rolling, overcoming internal challenges, building trust with champions, and creating massive buzz up and down and across the org chart to get the deal over the line.
Sponsor: https://orgcharthub.com/ Visualize your accounts, see key stakeholder roles, and understand relationships at a glance.
Show Notes
- Evan Intro & Background
- Deal Background & How it Started- When and how did you get connected with a Champion
- Competition and challenges
- How a $34M SaaS Deal gets Closed
- What makes Evan unique as a seller
Long form 90 minute podcast Evan did with Scott Ingram: Sales Success Stories Podcast Episode 56
https://top1.fm/episode-56-evan-kelsey-of-seismic-800-achievement-with-a-massive-deal/
The JOLT Effect: How High Performers Overcome Customer Indecision
https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

Sep 5, 2023 • 21min
Ep.4: From SDR Bootcamp Intern to Top Rep and SaaS Founder - with Mike Miranda, former GitLab AE and Current Founder, Optonal
Listen here for the fascinating background from SDR Bootcamp Intern to Top Performing Rep at GitLab and now Founder at SalesTech Startup Optonal.
Mike Miranda shares his insights from a memorable deal where multithreading, product usage signals, and a last second end of quarter deal led to a big outcome.
We cover the deal story and actionable tips and learnings, while also hearing Mike's unique selling style that blends effective communication (call-heavy) with a pursuit of excellence.
Connect with Mike on LinkedIn (https://www.linkedin.com/in/zmmiranda/) and explore OpTonal's innovative solutions for Gong, Google Meet, and Zoom users at OpTonal.com.
Link to Gitlab Handbook:
https://about.gitlab.com/handbook/

Aug 28, 2023 • 10min
Ep.3: How the Deal was Done | Selling $100k worth of Snacks to Financial Institutions with Byron Sierra-Mattos
Byron Sierra Mattos has an incredible career journey and appetite for learning.
After selling chocolate bars door-to-door, he landed his first SaaS job at fast-growing startup SnackNation. Here he leveled up his sales skills, became a top-performer, and closed a $100k deal in his last day at the company. From there he went on to sell at a unicorn, became a consultant, and is now bringing new sales tech to market at startup AlignedUp.
Give this episode a listen and be sure to connect with Byron-Sierra Mattos on LinkedIn.

Aug 28, 2023 • 13min
Ep.2: Selling Million Dollar Software Deals to Private Equity-backed Clients with Bullhorn's RVP of National Accounts Keith Weightman
Keith Weightman has been with Sales and Recruiting CRM Platform Leader Bullhorn for a decade.
This is an extraordinary tenure in the fast-changing and high-turnover tech industry.
Give a listen to hear about Keith's experience and expertise.
This episode is especially useful for sellers working with Private Equity-backed clients in the Enterprise segment.
Keith shares tips and learnings for how to maximize a deal and set up win-win outcomes.
You can connect with Keith Weightman on LinkedIn. And be sure to check out his newsletter and amazing resources on visual selling and whiteboarding.

Aug 25, 2023 • 13min
Ep.1: How the Deal was Done with OrgChartHub Founder Daniel Currin
Daniel Currin was the first sales hire at a UK-based startup. He led them to Product Market Fit and won a land and expand deal at one of the largest healthcare and medical device companies in the world ($170 Billion market cap). The deal gave the small startup momentum which led to a successful acquisition.
Off the back of the deal he gained experience that led him to found the OrgChartHub App in the HubSpot marketplace. Listen in to hear the story of “How the Deal was Done” and where it led to.
You can connect with Daniel Currin on LinkedIn and check out his app OrgChartHub which is key for visualizing the CRM and navigating complex deals https://orgcharthub.com/