Matt Caudill

Revenue Strategy and Operations Senior Analyst

Turquoise Health

Revenue OperationsRemote📍 Remote
Posted by Matt Caudill

Overview

You're the senior Rev Ops person (possibly the only one, or working alongside an Analyst) building out operations infrastructure for Sales, CS, and Marketing at a 164-person healthcare data company. You'll own bigger projects like redesigning the sales comp plan or building the quarterly forecast model, while also handling ongoing reporting and systems admin. This is a "build it from scratch" role where you'll have significant input on how they run revenue operations.


Role Snapshot

AspectDetails
Role TypeSenior Generalist Rev Ops - Sales/CS/Marketing
Sales MotionN/A - you support the team, don't sell
Deal ComplexityN/A - operational support role
Sales CycleN/A
Deal SizeN/A
Quota (est.)N/A - measured on strategic project delivery and systems maturity

Company Context

Stage: Likely Series A/B based on size (164 employees)

Size: 164 employees

Growth: Hiring for Rev Ops signals scaling the GTM motion - they need someone to professionalize their operations

Market Position: Healthcare pricing transparency space - technical product that requires education and likely involves complex sales to hospitals, payers, or health systems


What You'll Actually Do

Time Breakdown

Strategic Projects (40%) | Reporting & Analysis (25%) | Systems Management (20%) | Stakeholder Management (15%)

Key Activities

  • Designing compensation plans: Building the structure for sales/CS comp (quota relief, accelerators, bonuses), modeling financial impact, getting buy-in from leadership and reps
  • Forecasting and pipeline management: Building the weekly/monthly forecast process, training managers on pipeline hygiene, analyzing forecast accuracy to improve the model
  • Territory planning: Designing territory structure, building account segmentation logic, modeling capacity/coverage, handling the political conversations when someone loses accounts
  • Executive reporting: Building board-ready slides on revenue metrics, ARR growth, NDR, sales efficiency - needs to be polished and accurate
  • CRM architecture: Deciding what fields they need, how opportunity stages should work, what automation makes sense, which integrations to invest in
  • Process design: Creating playbooks for deal reviews, QBRs, forecasting calls - documenting how things should work rather than just fixing what's broken
  • Tool evaluation: When they need a new sales engagement platform or CS tool, you're scoping requirements and managing the vendor selection

The Honest Reality

What's Hard

  • You'll have opinions on how things should work, but leadership might override you - healthcare sales is complex and they know their business better than you do initially
  • "Building the plane midair" means every project you start will uncover three more problems you didn't know existed
  • Senior level means you're expected to have answers, but if they haven't had Rev Ops before, the data to support your recommendations might not exist yet
  • You'll spend time on tactical work (fixing Salesforce issues, one-off reports) even though you were hired for strategy - there's no one else to do it
  • Getting Sales, CS, and Marketing aligned on shared definitions (what's a qualified lead, when does Sales hand off to CS) is harder than the technical work
  • If they hire both an Analyst and Senior Analyst, you'll need to figure out who owns what without clear guidance since the roles aren't specialized yet
  • Healthcare means long sales cycles and complex deal structures - understanding how to measure success takes domain knowledge you'll need to build

What Success Looks Like

  • You've designed and rolled out a new comp plan that reps understand and Finance approves
  • Forecast accuracy improves from whatever mess it is now to +/- 10% by end of Q2
  • The exec team stops asking for custom reports because you've built dashboards that answer their questions
  • You've documented 5-10 key processes that become "how we do things"
  • When they hire specialized ops people later (Sales Ops, CS Ops), you've built the foundation they'll work from
  • Sales/CS leaders include you in strategic planning conversations, not just tactical execution

Who You're Supporting

Primary Stakeholders:

  • Revenue Strategy & Operations Manager (Matt Caudill - your direct boss)
  • VP Sales or Head of Revenue (strategic partner on GTM planning)
  • Head of Customer Success
  • Head of Marketing
  • CFO (for financial planning and commission expense)
  • CEO (for board reporting)

What They Care About:

  • Sales Leadership: Predictable pipeline, fair territories, comp plans that drive the right behavior, accurate forecasts
  • CS Leadership: Customer health visibility, renewal risk flags, expansion opportunity tracking
  • Marketing Leadership: Clear attribution model, lead quality metrics, ROI on campaigns
  • Finance: Revenue forecasts, commission expense tracking, clean data for audits
  • CEO: ARR growth, efficiency metrics (CAC, LTV, sales productivity), confidence in the numbers they present to the board

Requirements

  • 3-5+ years in Rev Ops, Sales Ops, or related analytics role (consulting or finance backgrounds can work if you've been customer-facing)
  • Expert-level Salesforce admin skills - you should be able to build custom objects, automation, and reports without help
  • Strong analytical skills - comfortable building financial models in Excel, doing SQL queries if needed, working with BI tools
  • Experience designing comp plans or other strategic ops initiatives, not just reporting
  • Ability to influence without authority - you'll need to get buy-in from leaders who don't report to you
  • "Humble and people smart" means you can handle pushback on your recommendations without getting defensive
  • Comfortable with ambiguity and building structure where none exists
  • Healthcare or other complex B2B SaaS experience helpful but not required