Kaela Olsen

GTM Strategy & Operations

Harvey

Revenue OperationsRemote📍 Remote
Posted by Kaela Olsen

Overview

You sit between Harvey's GTM leadership and the operational reality of scaling from 1,000+ customers to wherever they're headed next. You're building the models that inform comp plans, territory assignments, and capacity planning. You're also the person who gets pulled into every cross-functional fire drill when sales processes break or forecasting falls apart.


Role Snapshot

AspectDetails
Role TypeGTM Strategy & Operations
Sales MotionN/A - Internal Ops Role
Deal ComplexityN/A - Supporting Enterprise Sales
Sales CycleN/A
Deal SizeN/A
Quota (est.)N/A - Project Deliverables

Company Context

Stage: Late-stage growth (1,157 employees, 1,000+ customers)

Size: ~1,200 employees across 12+ global offices

Growth: Expanding internationally, hiring across GTM at scale

Market Position: Category leader in legal AI - selling into a traditionally slow-moving, risk-averse market (law firms and in-house legal teams)


GTM Reality

Who You Support:

  • VP/SVP Sales (probably multiple regional leaders)
  • CRO or Chief Revenue Officer equivalent
  • AE teams across enterprise, mid-market segments
  • Customer Success leadership

What They're Selling: Enterprise AI platform to Am Law 100 firms and F500 in-house legal teams. Deals are 6-12+ month cycles with procurement, security reviews, and change management hurdles. Reps need data, process clarity, and operational support to hit numbers.

Your Mandate: Build the infrastructure that lets GTM scale without falling apart. You're the one leadership calls when they need to understand pipeline coverage, model next year's headcount, or figure out why conversion rates tanked in Q3.


What You'll Actually Do

Time Breakdown

Data Analysis (35%) | Strategic Projects (30%) | Meetings (25%) | Admin/Firefighting (10%)

Key Activities

  • Territory & Capacity Planning: Building models in Excel/GSheets to figure out how many AEs they need in each region, what coverage ratios look like, and where to add headcount. You're pulling pipeline data, running scenarios, presenting recommendations to leadership.
  • Comp Plan Design & Modeling: Working with finance and sales leadership to model quota assignments, OTE structures, accelerators, and SPIFs. You'll run sensitivity analysis on what happens if ramp time changes or win rates drop.
  • Process Improvement Projects: When deals get stuck in legal review for 90 days or forecasting accuracy is 60%, you're the one mapping the broken process, interviewing stakeholders, and proposing fixes. Then you have to actually get people to adopt the new process.
  • Sales Analytics & Reporting: Building dashboards in Salesforce, Tableau, or Looker. You're tracking pipeline velocity, conversion rates by segment, rep performance, and whatever metric leadership is obsessing over this quarter. Lots of "can you pull this data by EOD" requests.
  • Strategic Initiatives: Ad-hoc projects like "should we open an office in Singapore," "how do we think about vertical specialization," or "model out what happens if we pivot our enterprise motion." These are high-visibility but poorly scoped.

The Honest Reality

What's Hard

  • Unclear Priorities: You'll have 5 exec stakeholders with different agendas. One wants headcount planning done, another needs pipeline analysis, a third just dumped a "quick question" that's actually a week-long project. You have to triage and manage up constantly.
  • Data is Messy: Salesforce hygiene is probably inconsistent. Reps don't update stages, dates slip without notes, and you'll spend hours cleaning data before you can even start analysis. "Garbage in, garbage out" is your reality.
  • Moving Targets: You'll build a beautiful territory model, then leadership changes the ICP or shifts the segment focus, and half your work is obsolete. The company is scaling fast, so strategy shifts frequently.
  • Execution Dependency: You can design the perfect process, but if AEs don't follow it or managers don't enforce it, nothing changes. You have influence but no direct authority over the field.

What Success Looks Like

  • Leadership starts trusting your models enough to make $10M+ headcount or comp decisions based on your work
  • You ship a process change (like new forecasting rigor) and adoption actually sticks at 80%+
  • Your pipeline analysis catches a trend early (like a segment dying or a new vertical heating up) and GTM pivots before it's a crisis
  • You become the "go-to" person for GTM questions - people Slack you instead of guessing or building their own broken models

Who You're Working With

Primary Stakeholders:

  • CRO / VP Sales: Setting strategy, need decision support and analytical firepower
  • Sales Leaders (Regional VPs, Directors): Want territory plans, quota models, performance insights
  • Finance: Partner on comp plans, headcount budgets, forecasting accuracy
  • Sales Ops / Systems Team: You own strategy/analysis, they own tools and day-to-day admin

What They Care About:

  • Accuracy: Your models need to be right. If you say they need 20 AEs and they hire them, you can't be off by 50%
  • Speed: Exec teams move fast. You need to turn around analysis quickly, even when the ask is vague
  • Actionability: They don't want a 40-slide deck. They want clear recommendations and next steps

Requirements

  • 3-5 years in Strategy, RevOps, or Management Consulting (MBB, Big 4, or boutique)
  • Strong in Excel/GSheets modeling - you should be able to build territory models, quota waterfalls, and capacity plans without hand-holding
  • Experience with Salesforce, and at least one BI tool (Tableau, Looker, etc.)
  • Consulting, banking, or PE/VC background - they want people used to ambiguous problems and exec-level stakeholder management
  • Comfortable context-switching between strategic ("should we enter APAC?") and tactical ("why did conversion rates drop 5% last month?")
  • Legal/professional services experience is a plus but not required - you'll learn the domain