[Hiring] GTM Systems Advisor @59 Pines

Role Description

We're hiring a GTM Technical Coach to audit, benchmark, and sharpen our go-to-market engine from the inside out.

Flexible Title: Can tailor to reflect your skills & experience.

Flexible Time: Can do full-time, part-time, side-gig (off-hours), or fractional (contract).

Flexible Commitment: Can do short-term, long-term, or intermittent.

Why so flexible? We're a FUNDED startup racing to launch end of Q2 2026. That gives us just 3 months to stack features while raising additional working capital. Feel free to jump in, help us ship, then bounce >> or stick around. A successful launch translates into lots of permanent jobs for those that want them. We're also interested in long-term "side gig" relationships, if that's what you're into—in our experience, a few expert hours often beat full-time learning-curve hours.

About The Role: We have a GTM motion running—channels are live, systems are connected, campaigns are in flight. What we don't have is an experienced external set of eyes to tell us where it's strong, where it's broken, and what realistic benchmarks look like. That's the gap this role fills.

This is a senior advisory and coaching seat that blends a systems integration background with deep, hands-on GTM engineering experience. You've built the workflows, run the campaigns, and iterated the sequences yourself—so when you look at someone else's stack, you immediately see what's working and what isn't. When the team says a campaign change will take two weeks, you know whether that's reasonable—because you've done the work yourself.

This is not a full-time execution role. We estimate 5–6 hours per week, primarily anchored around weekly GTM meetings with async follow-up. The role could evolve as the relationship develops—including potentially joining the team in a larger capacity.

You'll answer:

• Are our systems set up correctly?
• Are our timelines realistic?
• What does "good" actually look like compared to where we are?
• Where should we push harder, and where should we pivot?

Compensation

Up to $175,000 max total annual compensation in Tier 1 cities; cash and equity components to be negotiated (amount reflects combined cash and equity components). Given the expected time commitment (~5–6 hrs/week), comp will be structured accordingly—fractional or hourly arrangements welcome.

What You'll Do in Your First 60 Days

• You've audited our full GTM stack—tools, integrations, workflows, reporting—and delivered an honest assessment of what's strong, what's fragile, and what needs to change.
• You've established realistic time benchmarks for core GTM activities (ICP changes, persona updates, prompt iteration, campaign launches, enhancement rollouts) and those benchmarks are actively being used to set expectations.
• You've identified bottlenecks where implementation speed doesn't match what's being reported—and the team has a shared understanding of why.
• Leadership has better signal on campaign performance: what's real vs. what just looks good on the surface.
• You've helped the team navigate at least one pivot or major decision—when to kill a channel, when to iterate vs. rebuild, when timelines need to shift.
• You've built strong rapport with the team and they actively seek your input.

What You'll Do Ongoing

• Attend and participate in weekly GTM meetings—join the team's core weekly meetings, observe how work is discussed and planned, and provide real-time coaching and input.
• Coach through async follow-up—translate meeting discussions into actionable written feedback; surface what was missed, challenge assumptions, and help the team sharpen their thinking.
• Validate reporting and analysis—review how we're measuring campaigns; help us understand whether our metrics are meaningful and whether the story the data tells is accurate.
• Help the team problem-solve—identify when to pivot, when to push harder, when timelines are off, and when an approach needs to fundamentally change.

Qualifications

• You've done the work—you've personally built and run GTM systems in a hands-on engineering capacity; you can coach because you've been in the seat—not because you read about it.
• Systems integration background—understand how GTM tools connect, where integrations break, and how data flows between enrichment, outreach, CRM, and reporting layers.
• Startup experience, ideally ground-zero—built GTM motions from scratch at early-stage companies where nothing was defined; know what "normal hard" looks like vs. "something is actually wrong," and can spot the difference in someone else's operation.
• Strong async communicator—deliver clear, actionable written feedback without needing a meeting for every point; document your thinking and share it proactively.
• Honest and constructive communicator—give direct feedback with respect and context; the teams you've worked with trust you because you're straightforward and collaborative.

Requirements

• Experience with tools in our current stack: n8n, FullEnrich, Claude, Perplexity, PhantomBuster, LinkedIn Sales Navigator—though the stack evolves, so adaptability matters more than specific tools.
• Experience coaching or advising GTM teams (not just building for yourself).
• Familiarity with outbound deliverability, lead scoring, and campaign performance analysis.
• Venture-backed startup experience.

What You're NOT

• Not a full-time executor—the GTM Engineers handle day-to-day execution; you're here to audit, benchmark, coach, and challenge, not to run campaigns yourself.
• Not a strategist who's never built—we need someone who's done the hands-on work; pure advisors who haven't wired a workflow or debugged a deliverability issue won't have the credibility this role requires.
• Not a manager (today)—this role doesn't currently include people leadership or headcount decisions, though it could grow into that as the team and operation scale.