Accelerate Podcast with Andy Paul
September 22, 2017

#572. How to Hire the First Salesperson for a Startup. With Bridget Gleason.

Bridget Gleason is VP of Sales for and my regular partner on Front Line Fridays.


[2:57] Bridget brings a guest from Bianca Lewis was the first sales rep at is the third startup to bring Bianca in as the first sales rep. She joins a company with an unproven product and gives them a big lift.

[4:02] Bianca talks of the energy, the understanding, and the incredible dedication to the cause that such an endeavor involves. Bianca started at each startup after the Founders had dipped their toes in the market with their friend networks.

[7:01] Bianca says the invaluable initial skeleton of the system was in place. What Bianca did was to put flesh on those bones. She talked to her own network to find the value of the product to the prospect and developed the pitch from there.

[7:43] Bianca’s process: A startup has no brand against established competitors. Bianca turns that into an advantage by getting a firm grip on the technology, the market, and the value, and offering prospects a role in a new approach.

[9:14] Besides the flexibility of newness, there are pricing and support advantages, because there aren’t many clients yet. Success breeds success. After the first clients, Bianca talks about why clients are going with a new firm.

[9:47] The first salesperson is always the Founder/CoFounder. Bianca has the ability to recognize the pattern they establish, and apply it to the market beyond their network, starting with low-hanging fruit and building up a network as she goes.

[12:27] The pitch for the first customers is different than the pitch after you have gotten initial traction. The first signups need to see a low risk. Offer a one-month trial, not an annual contract, on a product two weeks old. Then hire talented reps.

[14:34] The initial sales reps will work closely with the lead seller until there is product stability. Bridget notes that Bianca is highly over-qualified, which makes her a good match for selling an evolving product, and stay involved in each sale.

[17:49] There’s a tendency to make the first sales hire the VP of Sales. Instead, hire someone who is more focused on achievement, but will add to the infrastructure in preparation for the hiring of a VP of Sales. Bianca discusses hiring errors.

[22:37] Bianca’s original title at was “Sales.” She is a pinch hitter without a large ego; good at everything with the trust of the founders and working long hours to get deals. Titles are incredibly restrictive in the initial stages of a startup.

[26:29] The initial salesperson who can demonstrate to the CoFounders their understanding of the product technology and how it will fit into companies will gain their trust and be able to build a good team. Bianca’s only focus is closing.

[29:50] When the VP of Sales is hired, as Bridget was, the question is what to do with the first salesperson. Bridget says to continue to empower them.

April 4, 2016

On Accelerate! Now: Episode 126 with Jorge Soto. You Can’t Replace The Human Element in Sales

Jorge Soto is the founder of Sales4Startups and a serial entrepreneur.  In this episode, Jorge drives the point home that it is essential, in this age of data, analytics and automation, to not forget about the human element in business in general, and in sales in particular.  Among the topics that Jorge and I talk about are:

  • What are some of the ‘sure things’ that don’t accelerate sales in start-ups?
  • Why it is essential that start-up founders and leaders need know how to sell their product or service.
  • Why it’s still the best strategy to focus on quality over quantity in lead development.
  • Why authentic relationships are still the best route to sales success.