Founding HRTech GTM Lead

Hybrid Remote/In-Office in Sydney, Australia · Founding hire

About Winslow

Winslow is the AI-native HR platform (payroll, benefits, HRIS, and automation) that finally lets HR teams build HR the way they want. While Winslow comes with everything you need out of the box, our AI-native architecture lets you extend the product with your favorite vibe coding tools and build workflows with agentic infrastructure.

We sell to early stage CEOs, small company HR leaders, and Fractional HR specialists working with 1–300 person companies. For smaller teams we bundle HR expertise as needed and for larger teams we bundle forward deployed agentic PeopleOps experts.

Today’s marketing is a combination of narrative, community and content organized into effective programs. As we are a platform built for HR builders, we’re heavily investing in educational content and marketing what our customers are doing on our platform.

Why Sydney

Our founder and CEO lives in Sydney with his family. While we are a US company we’re willing to find the best talent anywhere. You’ll be working directly with the CEO both remote and in-office in the CBD.

The role

You're our founding GTM Lead. You're not here to hit a quota — you're here to figure out the motion.

Think back to the first GTM hire at Gusto, Rippling, or Deel, sometime around their Series A. There was no playbook. There was a product, a thesis about who would buy it, and a person whose job was to find out by trying. Cold outbound. Founder-led selling and demos. Hand built communities that turned into full fledged certification processes. Whatever works, run twice. Whatever doesn’t, kill quickly.

That's the job. You'll own three motions in parallel, and figure out which one bends the curve:

Fractional HR Leaders. The growing layer of fractional HR consultants servicing 20–200 person startups. They're our natural channel — they have the relationships, they need better tooling, and they win when their clients run on Winslow. Sign them as partners. Educate them. Allow them to offer a different value prop (HR + Business Automation). Get them shipping Winslow into their books.
Startup Ecosystem: VC portco offers, accelerator sponsorships, hackathons, partner discount programs like Ramp/Brex. Be everywhere a founder is looking for insight into what to try and buy.
Direct outbound to startups. Preseed - Series A. US startups whose founders and ops leads are already AI-curious. You'll run the outbound, agentically — your prospecting, enrichment, and personalisation stack should look like a 2026 stack, not a 2022 one.

Across all three, you'll work agentically. We're an AI company. Our GTM Lead doesn't have an SDR — they have agents. You build your pipeline with the same kind of tooling our customers buy from us: outbound agents, research agents, CRM automations, intent signals stitched together with Clay/Apollo/Smartlead/whatever-comes-next. If "agentic GTM" is a phrase you've already been living for the last twelve months, this is your role.

You'll be our loudest voice into product on what partners need, what objections kill deals, and which segments are pulling. The GTM motion you design will shape the product roadmap as much as the other way around.

A typical week looks like:

Two or three partnership conversations with fractional HR firms or payroll providers — first pitches, follow-ups, deal structuring
A working session with our most active channel partner: helping them position Winslow, building a co-sell deck, tuning the referral flow
Running the agentic outbound stack: reviewing what your agents shipped overnight, tuning prompts, iterating on lists and personalisation
Founder-led sales calls with the warmest 2–3 inbounds — you run them, the founder joins when it helps
Synthesising what you learned into the GTM playbook so the next hire doesn't start from zero
Logging what's broken about Winslow for the segments you're hunting, back to product and engineering. Constantly. This loop is the company.
Occasional travel (~10%) for partner offsites and conferences when it's the right move

Who you are

Early at an HR tech company that scaled. You were employee #5 to #50 at a Gusto, Rippling, Deel, Employment Hero, Justworks, Remote, or similar — early enough that you watched the GTM motion get invented, ideally close enough to it that you helped invent it. You know what early-stage HR tech distribution actually looks like, not what it looks like once there's a 200-person sales org.
Agentic, not aspirational. You've already replaced large chunks of your own job with agents. Your outbound is half-built, half-bought. You can talk fluently about Clay, Apollo, Smartlead, Instantly, Lemlist, Attio, Common Room, and whatever's launched in the last six months. You're not waiting for an SDR — you are the SDR, with agents.
A channel and partnerships builder. You've signed channel partners before. You know how to structure a referral program, an integration partnership, a co-sell motion. You can sit with the founder of a 12-person fractional HR firm and walk out with a partnership agreement and a Slack channel.
A founder-grade communicator. You can do a first demo without a deck. You write outbound that doesn't sound like outbound. You can hold your own with a CFO, a People Ops leader, and the founder of a payroll bureau in the same week.
A systems thinker about distribution. You see funnels, segments, leading indicators. You instrument what you build. You can tell the founder, with data, which of the three motions is working — and kill the ones that aren't.
A loud feedback loop. You can't help noticing what's broken in the product you're selling. You write it up clearly. You push for it to be fixed.
Comfortable with ambiguity. This role doesn't exist anywhere else yet. You'll define it.
Bias to action, low ego, allergic to bureaucracy.

Nice to have

A public voice in the HR-tech or HR-AI conversation (LinkedIn, podcast appearances, community membership, conference talks)
An existing network in the US fractional HR, or payroll ecosystem
Hands-on experience building or operating channel/partner programs at an early-stage SaaS company
Familiarity with the major HRIS, payroll, and ATS platforms you'll be selling around (Employment Hero, BambooHR, Workday, Rippling, Gusto, Greenhouse)
Prior founding-GTM-hire experience at another startup

Compensation and benefits

Base + superannuation, no variable
Meaningful early-stage equity
Hybrid remote + in-office in Sydney
Top-tier tools, no procurement gauntlet
The chance to build the GTM motion for an AI-native HR company from zero

We've deliberately built this as a base with no-commission role. We want a builder, not a quota-chaser. The right person will define the motion that future quota-carrying hires inherit. We are not sponsoring work visas at this time.

How to apply

Send us a short note — no cover letter, please — about an outbound, partnership, or channel motion you've built and what insight you’ve learned about marketing into HR tech right now. Bonus points if agents did most of the work. What was the thesis, what did you ship, what worked, what didn't, and what would you do differently the second time. We respond to everyone who takes the time to spin this up for us.

Winslow

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Founding HRTech GTM Lead