Scott Leese

Venture Partner & LP, TipTop VC
Scott Leese is a hands-on sales operator who pushes founders to build sales structure, creates community through Surf & Sales and Thursday Night Sales, hosts a podcast, with unicorn exits.
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Scott Leese
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AI
SaaS
Fintech
Enterprise
Health
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About Scott Leese

Scott Leese built his reputation as a hands-on sales operator rather than a traditional investor, shaped by a serious health battle in his 20s and a late start in sales at age 27, and he's known for pushing early-stage founders to build real sales structure instead of winging it. He's also built a public brand around community and content, connecting sales to surfing through Surf & Sales and Thursday Night Sales, hosting one of the most active podcasts in the sales world, and drawing on hands-on experience with numerous unicorns and exits.

Scott Leese's Interests

What they've been talking about across their social media accounts
  • A strong emphasis on refining sales processes and leadership. Believes that simply increasing call volume will not fix a broken system, and teams should instead focus on repairing the weakest parts of their pipeline. Points out a major disconnect between leaders who think they are coaching and reps who feel unsupported, noting that assigning a quota is not a substitute for uncovering true motivation. For instance, advises that if a prospect has to ask what happens next on a call, the salesperson has already lost control of the conversation and is merely following rather than leading.
  • Values founders who prioritize sustainable growth over vanity metrics and external validation. Believes that tying success to arbitrary markers like job titles or the size of a fundraising round means letting others dictate your worth. Warns against spending time on enjoyable tasks rather than the difficult work that actually drives the business forward. For example, notes that losing a massive, recognizable client early on is actually one of the best things that can happen to a startup that is not ready to handle it, and encourages tracking the hidden emotional and time costs of difficult clients rather than just the raw revenue they bring in.
  • An appreciation for intentional networking and audience-focused branding. Suggests that a personal brand should be built entirely around a specific problem solved for an audience rather than just promoting oneself. Stresses the importance of a robust digital network, expressing disbelief that modern revenue executives could have small online footprints. Highlights the value of serendipitous encounters, using the example that ideas move much faster in dense cities than in suburbs because spontaneous conversations often lead to unexpected solutions from people in entirely different roles.
  • Promotes combining personal passions with professional growth to create better environments for success. Repeatedly advertises a mastermind event in Costa Rica that merges surfing with sales training for founders and sales leaders. Argues that placing yourself in the right room can alter your career trajectory far faster than raw motivation, and urges professionals to stop passively watching others take risks and instead actively put themselves in challenging or novel situations.

About their Fund

Sectors
AI, SaaS, Fintech, Enterprise, Health
Rounds
Pre-Seed - Seed
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TipTop VC focuses specifically on vertical AI, betting that the bigger opportunity lies in replacing labor and services budgets rather than software budgets, and it backs founders building in overlooked industries like legal, home services, construction, agtech, K-12 payments, freight, and financial advice. The fund is run by Nick Tippmann, a former vertical SaaS operator, and is backed by a group of LPs who previously built companies like ServiceTitan, Procore, Mindbody, and Greenlight Guru, giving founders access to people with direct experience scaling vertical software companies, along with support on go-to-market strategy and hiring.

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