When selling to large companies, young founders often mistakenly adopt a formal, corporate persona. This is a mistake. Enterprises are often buying the startup's unique energy and expertise, so being authentic and passionate is more effective than mimicking corporate culture.
Related Insights
New entrepreneurs often hide their personality, believing their work should stand alone. This stems from imposter syndrome and a desire to blend in. However, clients connect with the person behind the brand first. Hiding yourself is a disservice that prevents the trust and differentiation needed to build a loyal audience.
At the $1-10M ARR stage, avoid junior reps or VPs from large companies. The ideal first hire can "cosplay a founder"—they sell the vision, craft creative deals, and build trust without a playbook. Consider former founders or deep product experts, even with no formal sales experience.
A successful startup often resembles a cult, requiring a leader who communicates their vision with unwavering, first-person conviction. Hiding the founder behind polished PR spokespeople is a mistake; it neuters the contagious belief required to recruit talent and build a movement against impossible odds.
Enterprise leaders aren't motivated by solving small, specific problems. Founders succeed by "vision casting"—selling a future state or opportunity that gives the buyer a competitive edge ("alpha"). This excites them enough to champion a deal internally.
Sellers often adopt an overly formal, academic persona when speaking to executives, which creates distance. In reality, executive conversations are simple, direct, and unpretentious. Drop the jargon and complicated words. Your goal is clear communication, not demonstrating your vocabulary.
The nature of marketing has shifted from promoting a faceless corporation to showcasing an authentic founder personality. Companies without an interesting character at the helm are at a disadvantage. This requires leaders to be public figures, as their personal brand, story, and voice are now integral to the company's identity and success.
Startups can't compete with established leaders on credibility, but they have a unique advantage: access. Position your offer not as being "better," but as providing direct contact with the founder, contrasting it with the impersonal, multi-layered support of a large corporation.
Your ideal champion inside a large company is often someone who secretly wishes they'd founded a startup but is too risk-averse. They are drawn to the founders' ambition and will advocate for you because they want to feel part of the startup journey vicariously.