How the Deal was Done | Deal Stories Podcast

Jacob Karp, a seasoned enterprise sales expert with a dynamic background in journalism, media, public relations, and a decade in enterprise sales joins Andrew Kappel for this installment of How the Deal Was Done. The episode delves into a significant deal with a Fortune 200 telecommunications company, revealing Jacob's strategic approach to expanding an existing account, overcoming challenges,...

Want to hear a $7-figure deal story where the seller NEVER met anyone at VP or higher? Ever wonder what happens with your slides that you prepare for the champion? Want to learn how to buy something you’ve never bought before and de-risk the vendor race? If so, this is a can’t miss episode about a buyer and seller that did multiple $7-figure enterprise deal to generate 8-FIGURES-WORTH-OF-REVENUE t...

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’...

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...

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 inte...

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! #...

# 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...

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 par...

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 : Se...

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 t...

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...

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 tech...

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 da...

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 I...

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'...

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. Spons...

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 g...

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 opport...

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 uniqu...

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...

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 ho...

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...