Job Description

3 days ago Be among the first 25 applicants

Compensation : $185K–$220K base + 50/50 OTE split ($350K–$400K OTE)

Equity: 0.75%

Category : B2B SaaS | Retail Tech | POS | Supply Chain

Stage: Series B ($20M raised)

Founded: 2019

Hiring Timeline: ASAP - aiming to hire within 4 weeks

The Company

This US-based SaaS company is building a modern operating system that powers independent retailers through an AI-driven point-of-sale (POS), inventory management, and operational platform. They help grocers make smarter decisions around buying, pricing, merchandising, staffing, and collaboration.

They’ve just closed a $20M Series B and scaled to $2M ARR in under 12 months. Now they’re gearing up to 10x that growth and are looking for a Head of Sales to lead the next chapter.

Headquartered in San Francisco, with a distributed team and hybrid setup, they operate in the logistics, e-commerce, and AI-powered retail SaaS space.

The Team

Founded by Stanford engineers with backgrounds at SpaceX, Google, and Facebook, the company is backed by a world-class team of operators, advisors, and investors.

They’re proudly diverse, highly ambitious, and deeply mission-driven, combining technical precision with a passion for food, retail, and solving real-world problems.

The Mission

Their goal is to digitise the food supply chain.

This means empowering underserved, independent grocery businesses with the same tools used by giants, and helping them survive and thrive in a margin-tight, ever-changing world.

They’re going after a $10B+ market that’s been ignored and left behind by legacy vendors. It’s a category-defining opportunity.

The Role

As Head of Sales, you’ll architect and execute the full GTM strategy, lead and scale a high-performing field sales team, and partner directly with the CEO to take the business from $2M to $20M ARR by 2026.

This is not a cushy inside sales job. 50% of deals happen in-store, on loading docks, or in the back office between deliveries. They need someone with true field sales DNA who can lead from the front, close deals in the trenches, and build a culture of grit, pace, and performance.

Why This Role Matters

• This hire will determine whether they hit growth targets over the next 2 years.
• You’ll be their first true GTM architect - building process, team, and strategy from scratch.
• You’ll own the pipeline, process, people, and performance, reporting directly to the founders.
• You’ll step into a leadership role with real autonomy, clear upside, and impact at speed.
• There’s no safety net, but a huge opportunity to define success in a deeply underserved market.

Ideal Candidate Profile

Must-Have Background

• 10+ years in high-velocity SMB SaaS sales
• VP or Senior Director level in Series A-C startups or scale-ups
• Experience building and leading field sales teams of 10–100+ reps
• Proven track record growing ARR from $5M to $40M+
• Hands-on leader - capable of selling and scaling at the same time
• Experienced in $20K–$60K deal sizes, 2–6 week cycles
• Has led expansion across multiple US geographies
• You’re a Quota Crusher - 100%+ attainment is standard, not special

Bonus Experience

• Former founder, early-stage leader, or builder with a 0→1 mindset
• POS, fintech, or restaurant-tech exposure
• Technical fluency with CRM, metrics, dashboards, and AI tools
• Understands retail sales psychology and small business customer behaviour

Mindset & Attributes

• Strategic + Tactical: You build the plan and run the play
• Player-Coach: You set the tone by doing the hard things first
• Exceptional Communicator: You can win over sceptical operators and cross-functional execs
• Mission-Aligned: You care about food, community, tech, and fairness in business
• Customer-Obsessed: You don’t just pitch - you solve
• Culture Carrier: You build high-velocity, high-accountability, low-BS teams

This Role Is Not For You If:

• You’ve only sold to enterprise
• You’re allergic to field sales
• You’ve never hired or scaled a GTM team
• You need a full enablement team to function
• You can’t personally close a deal

Ideal Background Companies (for reference only)

• Food/POS SaaS: Toast, Clover, OpenTable, Owner.com, Square, Lightspeed, Uber Eats
• Fintech: Stripe, Brex, Ramp, Affirm

Interview Process

• Chat with CEO
• Founder interviews (COO + Strategic Lead)
• Take-home mock pitch – includes:Grocery store pitch, 10x growth plan, Leadership case study
• Final challenge panel with all founders
• Offer

How to Apply

If you’re a founder-mindset operator ready to build from the ground up, pitch like a top AE, and scale like a GTM architect, we’d love to meet you.

Apply via GTM Digital

We are running this search. We specialise in high-growth GTM recruitment for SaaS, AI, and venture-backed scale-ups across the APAC and US regions.

Apply now or DM [Justin Blij] for a confidential chat.

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Staffing and Recruiting

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