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When a deal takes two years - Unsloppable GTM with Leonard Burger
We explore the art and science of building a Go-To-Market strategy in B2B fintech with lessons that are applicable across industries, with someone who’s done it before and has spent years perfecting it.
The 100-words AI summary
Because we reckon with the usefulness of AI.
Leonard Berger explains how complex fintech enterprise deals can involve many stakeholders, take up to two years, and require a repeatable go-to-market (GTM) system rather than one-off selling. Using wholesale financing platforms as an example, he describes selling to finance providers while engaging dealership groups and OEMs, often replacing error-prone Excel-based processes. Success depends on sustained sales enablement: coordinated messaging, targeted account selection, and ongoing collateral—especially video—delivered at the right stages so momentum survives staff turnover and stalled deals. He also notes startups run two parallel sales cycles: selling customers and convincing investors. Visibility across channels builds trust, which ultimately closes deals. He advises product marketing bridge product, sales, marketing, and customer success, with a dotted-line structure across leadership.
Resources
This episode was produced by Orama - thought leadership videos: https://orama.tv/
We build thought leadership video assets for those selling complex products or services to enterprise buyers: human content for institutional solutions.
Leo and I met via the Fintech Marketing Hub who organise their flagship Fintech Marketing Conference on 30 June.
About Leonard Burger
Certified Product Marketing Manager (CPMM), Exec MBA, and angel investor navigating the intersection of growth strategy, fintech innovation, and venture building.Please contact me for anything related to: 👉 building high growth GTM engines, especially within fintech 👉 AI Venture building and investing 👉 startup, scaling and funding advisory
Connect on LinkedIn : https://www.linkedin.com/in/leonardburger/
About George Aliferis
George Aliferis is the founder of Orama. He spent over a decade in institutional finance before moving into media to build the bridge he couldn’t find: content that makes complex solutions visible and engaging.
Connect on LinkedIn : https://www.linkedin.com/in/george-aliferis/
About the Unsloppable podcast:
The show about enterprise sales in serious industries. Each episode, George Aliferis talks to commercial and marketing leaders in regulated, high-stakes markets about what actually moves complex deals — where thought leadership earns its place, and how they’re holding the line against the flood of AI-generated content drowning everyone else out.
Unsloppable: how human intelligence wins.
Timestamps
00:00 What complex deals in B2B fintech look like03:06 The long cycle of Tech against spreadsheets05:39 Startups’ dual sales cycles08:32 GTM as Infrastructure12:34 Org Structure For GTM15:16 Product Marketing Bridge Role18:03 A dotted line reporting model18:44 Wrap up
Thanks for reading Orama | Insight to Impact! This post is public so feel free to share it.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit oramatv.substack.com
View all episodes
By how complex beats slop in enterprise dealsWe explore the art and science of building a Go-To-Market strategy in B2B fintech with lessons that are applicable across industries, with someone who’s done it before and has spent years perfecting it.
The 100-words AI summary
Because we reckon with the usefulness of AI.
Leonard Berger explains how complex fintech enterprise deals can involve many stakeholders, take up to two years, and require a repeatable go-to-market (GTM) system rather than one-off selling. Using wholesale financing platforms as an example, he describes selling to finance providers while engaging dealership groups and OEMs, often replacing error-prone Excel-based processes. Success depends on sustained sales enablement: coordinated messaging, targeted account selection, and ongoing collateral—especially video—delivered at the right stages so momentum survives staff turnover and stalled deals. He also notes startups run two parallel sales cycles: selling customers and convincing investors. Visibility across channels builds trust, which ultimately closes deals. He advises product marketing bridge product, sales, marketing, and customer success, with a dotted-line structure across leadership.
Resources
This episode was produced by Orama - thought leadership videos: https://orama.tv/
We build thought leadership video assets for those selling complex products or services to enterprise buyers: human content for institutional solutions.
Leo and I met via the Fintech Marketing Hub who organise their flagship Fintech Marketing Conference on 30 June.
About Leonard Burger
Certified Product Marketing Manager (CPMM), Exec MBA, and angel investor navigating the intersection of growth strategy, fintech innovation, and venture building.Please contact me for anything related to: 👉 building high growth GTM engines, especially within fintech 👉 AI Venture building and investing 👉 startup, scaling and funding advisory
Connect on LinkedIn : https://www.linkedin.com/in/leonardburger/
About George Aliferis
George Aliferis is the founder of Orama. He spent over a decade in institutional finance before moving into media to build the bridge he couldn’t find: content that makes complex solutions visible and engaging.
Connect on LinkedIn : https://www.linkedin.com/in/george-aliferis/
About the Unsloppable podcast:
The show about enterprise sales in serious industries. Each episode, George Aliferis talks to commercial and marketing leaders in regulated, high-stakes markets about what actually moves complex deals — where thought leadership earns its place, and how they’re holding the line against the flood of AI-generated content drowning everyone else out.
Unsloppable: how human intelligence wins.
Timestamps
00:00 What complex deals in B2B fintech look like03:06 The long cycle of Tech against spreadsheets05:39 Startups’ dual sales cycles08:32 GTM as Infrastructure12:34 Org Structure For GTM15:16 Product Marketing Bridge Role18:03 A dotted line reporting model18:44 Wrap up
Thanks for reading Orama | Insight to Impact! This post is public so feel free to share it.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit oramatv.substack.com