

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

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/


