Terry Lee

Revenue Strategy & Operations Manager

Decagon

Revenue OperationsBalancedEnterpriseRemote📍 Remote
Deal Size: $100K-500K ACV
Sales Cycle: 3-6 months
Posted by Terry Lee•

Overview

You're focused on the strategic and analytical side of revenue operations—less systems administration, more planning and analysis. You build territory models, analyze funnel metrics, design compensation structures, and run ad-hoc projects for sales leadership. This is heavy Excel/Google Sheets work with regular presentations to GTM leaders.


Role Snapshot

AspectDetails
Role TypeStrategy-focused Rev Ops IC
Sales MotionSupporting enterprise AI platform sales
Deal ComplexityEnterprise consultative deals
Sales Cycle3-6 months
Deal Size$100K-500K+ ACV (estimated)
Quota (est.)N/A - measured on project delivery, analysis quality

Company Context

Stage: Series B/C (estimated based on 309 employees)

Size: 309 employees

Growth: Building out specialized Rev Ops function, moving beyond just systems admin

Market Position: Challenger in AI customer service space, competing on customization and multi-channel capabilities


GTM Reality

Pipeline Sources:

  • Mix of inbound (AI market interest) and outbound (proactive targeting)
  • Selling AI agents to enterprise customer service teams

SDR/AE Structure: Likely dedicated SDR team with AE handoffs

SE Support: Probably have SEs for technical demos and POCs


Competitive Landscape

Main Competitors: Other AI customer service platforms, traditional support tools adding AI features, internal AI builds

How They Differentiate: Voice/chat/email coverage, customizable AI personality, natural language workflow definitions

Common Objections: AI accuracy concerns, integration complexity, build vs. buy debates

Win Themes: Fast implementation, brand consistency, enterprise-grade customization


What You'll Actually Do

Time Breakdown

Data Analysis (40%) | Strategic Projects (30%) | Planning/Modeling (20%) | Meetings/Presentations (10%)

Key Activities

  • Territory Planning: Build models for how to carve up accounts among reps. Analyze account potential, rep capacity, geographic coverage. Present recommendations to sales leadership. Then adjust when they disagree with your logic.
  • Sales Productivity Analysis: Pull data on conversion rates, sales cycle length, win rates by segment/rep/source. Build dashboards showing where the funnel leaks. Present monthly business reviews with insights and recommendations.
  • Compensation Design: Model out quota attainment scenarios, design SPIF structures, analyze comp plan impact on behavior. Work with finance on budget implications. Field questions from reps about "what if" comp scenarios.
  • GTM Strategy Projects: One-off analyses for exec team—should we enter a new segment? What's our ideal customer profile? What's our sales capacity? Build financial models, analyze market data, make recommendations.
  • Forecasting Support: Help build forecast models, analyze pipeline health, identify risk deals. Weekly forecast call prep pulling data and building slides.
  • Process Documentation: Write playbooks for territory assignment, quota setting, lead routing. Nobody reads them, but leadership wants them to exist.

The Honest Reality

What's Hard

  • Analysis paralysis: You can spend weeks perfecting a model that leadership will decide differently on based on gut feel. Your beautiful territory model gets adjusted because a VP wants to protect their favorite rep.
  • Constantly shifting priorities: You'll be deep in one project when leadership asks for urgent analysis on something completely different. Your project list never shrinks.
  • Data quality issues: Every analysis starts with cleaning messy data. "Why are these opportunities in the wrong stage?" "Why isn't close date updated?" You'll spend hours making data usable before you can analyze it.
  • Stakeholder management: Sales leaders all want different things. You'll build something for one VP, then another VP asks why you're not measuring it differently. Lots of "managing up" required.
  • Repetitive reporting: Monthly business reviews, quarterly planning, weekly forecast prep—same analyses with updated numbers. The strategic projects you want to do get squeezed out by recurring reporting obligations.

What Success Looks Like

  • Territory model rolled out for new fiscal year and reps aren't revolting
  • Quota attainment across the team is 60-70% (healthy distribution, not too many at 0% or 200%)
  • Sales leadership references your analyses when making decisions
  • Forecasting methodology is trusted and accurate within 10%
  • Shipped 2-3 strategic projects per quarter that influenced GTM strategy

Who You're Supporting

Internal Stakeholders:

  • Head of GTM Strategy (your skip-level) - wants strategic insights
  • Sales VPs/Directors - want territory and comp recommendations
  • Senior Manager Rev Ops (your manager) - needs project execution
  • Finance - needs models for budget planning
  • Exec team - wants market analysis and strategy recommendations

What They Care About:

  • Sales leadership: Fair territories, achievable quotas, data-backed decisions
  • Finance: Accurate capacity models, budget implications
  • Executives: Market opportunity sizing, strategic recommendations
  • Rev Ops leader: Reliable project delivery, quality analysis

Requirements

  • 3-5 years in Revenue Operations, Sales Strategy, or related analytical role
  • Advanced Excel/Google Sheets skills—pivot tables, VLOOKUP, complex modeling in your sleep
  • Experience with Salesforce reporting and data analysis
  • Built territory models, quota plans, or capacity models before
  • Comfortable presenting analysis to senior leadership
  • SQL or BI tool experience (Tableau, Looker, Mode) is a plus
  • B2B SaaS experience, ideally with complex enterprise sales
  • Can work independently on ambiguous projects with minimal direction
  • Comfortable challenging assumptions—you'll need to push back when analyses don't support requested conclusions