Head of Sales

Head of Sales About the role

We're looking for our first Head of Sales to build, lead, and scale new logo revenue on sells AI software that automates document-heavy underwriting and back-office workflows for specialty finance - SMB funders, brokers, equipment finance and commercial insurance companies. We're past $13M in ARR and growing quickly; this role owns the road to $40M and beyond. You'll partner day-to-day with Jamie (co-founder and CRO) and work closely with product and engineering to build and lead the sales org as we grow.

Two things to know before you apply: this is a full-time,
in-person role in our NYC office (most of the team is in every day), and it's a hands-on,
player-coach seat - you'll carry a quota yourself while scaling the team.

This is a hands-on ("player-coach") role focused on driving revenue and building the sales function, including specifically:

• Lead our existing team of AEs and SDRs - a small, high-slope group who came into sales from non traditional backgrounds - and hire, onboard, and coach the next wave as we scale

• Develop and refine Heron's sales motion (ICP, messaging, pricing, deal structure, sales stages)

• Partner closely with founders, product, and engineering to translate customer pain into clear value propositions

• Build and manage pipeline, forecasts, and revenue targets with a strong bias toward accuracy and accountability

• Establish and refine our sales processes, tooling, and metrics (CRM, reporting, enablement materials)

• Help shape broader go-to-market strategy across sales, partnerships, and potentially customer success

This role is a great fit if you want back into the messy, high-ownership stage: ~$13M on the way to $50M, deals where product sits at the table with you, a young team you get to shape. It s the wrong fit if what you re after is a mature brand, a finished playbook, remote flexibility, or a pure people-management seat.

Our ideal hire will:

Have done our stage before

You were a member of or helped lead a sales org from under ~$12M to over $40M ARR (the more the better). We're equally interested if you were a top AE or front-line manager through that journey and have held sales leadership since - what matters is that you ve seen the road we re on. A long career at big, mature companies without early-stage scar tissue is unlikely to be the right background.

One more thing: revenue here means ARR.

Love selling and building at the same time

You're energised by being in the deals - especially early, messy ones - and you're excited to build structure after learning what actually works. You're comfortable wearing many hats and know how to prioritise impact over polish in the early days.

Have strong early-stage sales instincts

You know how to sell ambiguous, technical products without relying on heavy brand recognition or mature processes. You're thoughtful about deal qualification, pricing, and positioning, and you learn quickly from wins and losses.

Be scale-minded, but action-oriented

You don't over-engineer sales processes too early, but you do think ahead. You care about building something that will scale - and you know when it's time to formalise, document, and hire.

Be a clear, credible communicator

You can talk to technical and non-technical stakeholders alike, earn trust quickly, and clearly articulate value to customers, investors, and internal teams. Our buyers are C-level at specialty finance companies; you'll need to be credible with a CEO and a head of underwriting in the same meeting.

Here are some of the behaviours we expect of all Herons:

Scrappy and creative

When faced with a tough prospect, stalled deal, or unclear path…