Head of Revenue Operations

Overview

You're the Head of RevOps for Courser's portfolio of 20+ Managed Service Provider companies. You sit at the holding company level and build scalable revenue operations frameworks that get deployed across the portfolio. You spend your time standardizing CRM processes, building reporting dashboards for portfolio leadership, identifying best practices from high-performing MSPs, and working with individual company GMs to implement changes.

Role Snapshot

Company Context

Stage: Private Equity-backed portfolio (20+ companies)

Size: 197 employees at holding company level, likely 1,500-2,000+ across portfolio

Growth: PE value creation play - focused on operational excellence and multiple expansion

Market Position: MSP aggregator model - buying and consolidating managed IT service providers

GTM Reality

You're not running a single GTM motion - you're standardizing operations across 20+ different ones. Each MSP likely has:

• Mix of inbound (referrals, website leads) and outbound
• Different service offerings (some pure infrastructure, some M365-focused, some cybersecurity)
• Different deal sizes ($2K MRR contracts to $50K+ enterprise deals)
• Different tech stacks and levels of CRM maturity

Your job is to find common ground and build systems that work for most of them without being too rigid.

Competitive Landscape

Main Competitors: Each portfolio MSP competes with local/regional MSPs, national players like Dataprise, Converged, Impact Networking, and in-house IT teams

How They Differentiate: Industry specialization (financial services, healthcare, manufacturing) and local market presence

Common Objections: "Our current MSP is fine", pricing concerns, switching costs and migration fears

Win Themes: Proactive support vs reactive break-fix, industry expertise, cybersecurity capabilities

What You'll Actually Do

Time Breakdown

Stakeholder Management (30%) | Systems & Process (35%) | Reporting & Analysis (25%) | Strategic Projects (10%)

Key Activities

• CRM Standardization: You're getting 20+ companies onto consistent Salesforce/HubSpot configurations. Some are on spreadsheets, some have customized instances that don't talk to each other. You build the standard object model, fields, stages, and automation, then work with each company to migrate. Lots of change management and "but we do it differently here" conversations.

• Portfolio Reporting: You build dashboards for PE sponsors and Courser leadership showing pipeline, bookings, churn, expansion across all companies. You standardize definitions (what counts as a qualified opportunity? when is revenue recognized?) and consolidate data from 20+ sources. You spend time cleaning data and explaining why Company A's numbers don't match what they reported last month.

• Best Practice Identification: You analyze which MSPs are outperforming on sales velocity, close rates, or retention. You figure out what they're doing differently (better discovery process, different pricing model, tighter QBRs) and package it into a playbook. Then you run workshops to train other GMs and sales teams on it.

• Tool Rationalization: You audit the tech stack across the portfolio. Some companies have LinkedIn Sales Navigator, some don't. Some use Gong, some use Chorus, some have nothing. You make build vs buy decisions on which tools to standardize, negotiate enterprise contracts, and manage rollout.

The Honest Reality

What's Hard

• Herding Cats: Each MSP has a GM who thinks their market is different and your standard process won't work for them. You're constantly negotiating and getting buy-in. Some GMs are entrepreneurial founders who built the business their way - they don't love being told to change.

• Data Quality is Terrible: You inherit 20 CRM instances with inconsistent data entry, different field definitions, and no clean records. Before you can build good reporting, you spend months cleaning data and enforcing new standards. Sales reps at portfolio companies push back on "extra admin work."

• Limited Direct Authority: You don't manage the portfolio company teams. You influence through the PE sponsors and Courser leadership. If a GM doesn't want to adopt your process, you need to build the business case and get executive pressure. It's slow.

• Firefighting vs Strategy: You want to build strategic frameworks, but you're constantly pulled into "why did Company X's numbers drop?" or "the CRM integration broke" or "we need a custom report for the board meeting tomorrow."

What Success Looks Like

• You get 15+ portfolio companies on a standardized CRM setup with clean data and consistent processes within 12-18 months
• Portfolio leadership can see real-time pipeline and forecast across all companies without asking for manual reports
• You identify and scale 2-3 best practices that measurably improve conversion rates or sales velocity across the portfolio
• You reduce tech spend by 20-30% through enterprise licenses and tool consolidation

Who You're Working With

Internal Stakeholders:

• PE sponsors and Courser C-suite (you report here - they want visibility and proof of value creation)
• Portfolio company GMs (you influence them - they want autonomy and support that actually helps their numbers)
• Portfolio company sales leaders and RevOps teams (you work with them day-to-day - they're skeptical of holding company mandates)
• Deal teams evaluating new MSP acquisitions (they want your input on systems and integration)

What They Care About:

• PE Sponsors: EBITDA improvement, multiple expansion, clean data for exit
• GMs: Hitting their revenue targets, not breaking what's working, not adding admin burden to their teams
• Sales Leaders: Tools that actually help them sell, not just reporting overhead

Requirements

• 7-10+ years in revenue operations, with at least 3-5 years in leadership roles
• Experience in multi-company environments (holding company, PE portfolio, or rapid M&A integration)
• Deep Salesforce or HubSpot expertise - you've built instances from scratch and managed complex migrations
• Strong stakeholder management skills - you know how to influence without authority and build consensus across competing priorities
• Data analysis and visualization skills (SQL, Tableau/Looker, Excel modeling)
• Background in B2B services or MSP/IT services is highly preferred - you understand the sales motion and can speak the language
• Comfort with ambiguity and scrappiness - this isn't a 500-person RevOps team with specialized analysts. You're building the plane while flying it.