VP of GTM Strategy & Operations

Overview

You're architecting Chief's next-generation revenue engine as they modernize their GTM systems and scale their membership network. You'll own the full tech stack (CRM, enrichment, routing, revenue intelligence), build AI-powered automation, and partner directly with C-suite leadership on growth strategy. This isn't a pure systems admin role - you're setting the strategic direction while also building the actual infrastructure.

Role Snapshot

Company Context

Stage: Growth stage (6+ years old, backed by Primary Venture Partners and others)

Size: Unknown exact headcount, but operates 10,000+ member network with physical clubhouses across US

Growth: Expanding physical footprint, investing heavily in GTM infrastructure modernization

Market Position: Category leader in executive women's networking, strong brand recognition (77% of Fortune 100 represented)

GTM Reality

Pipeline Sources:

• Inbound referrals from existing members (high-intent)
• Outbound recruitment targeting senior women executives at specific companies/titles
• Event/programming-driven leads from workshops and executive coaching
• Corporate partnerships with Fortune 100 companies

Structure: You're building the infrastructure that powers membership sales and retention teams. There's likely a mix of membership recruiters (like SDRs) and account managers handling existing members.

Current State: Systems are being modernized - this means you're inheriting technical debt, fragmented data, and manual processes. Your job is to fix it.

Competitive Landscape

Main Competitors: YPO (Young Presidents' Organization), Vistage, other executive networking groups, traditional executive coaching services

How They Differentiate: Women-only, senior-level focus (40% C-suite), combination of peer networking + coaching + physical spaces, strong Fortune 100 penetration

Common Objections: "I'm already in [other network]", "I don't have time for another commitment", "What's the ROI?", pricing concerns for smaller companies

Win Themes: Peer connections at actual decision-maker level, proven ROI on career advancement, community of women who actually get it, programming quality

What You'll Actually Do

Time Breakdown

Systems Architecture (35%) | Hands-on Building (30%) | Strategic Planning (20%) | Cross-functional Meetings (15%)

Key Activities

• CRM & Data Infrastructure: You're auditing and rebuilding Salesforce configuration, fixing data quality issues, implementing enrichment workflows (ZoomInfo, Clearbit, etc.), and building routing logic for lead assignment. Lots of time in Salesforce setup, field mapping, validation rules.

• AI & Automation: Identifying opportunities for AI-powered workflows - could be anything from lead scoring to automated outreach sequencing to renewal risk prediction. You're evaluating vendors, building POCs, and implementing tools.

• Revenue Intelligence: Setting up dashboards, pipeline reporting, forecasting models, and performance analytics. You're building the systems that tell leadership what's actually happening in the revenue engine.

• Cross-functional Partnership: Weekly syncs with sales leadership, marketing ops, finance, and C-suite. You're translating business needs into technical requirements and vice versa. Lots of alignment meetings and stakeholder management.

• Process Design: Documenting workflows, building playbooks, training teams on new systems. When you implement a new tool or change routing logic, you're responsible for adoption.

The Honest Reality

What's Hard

• Rebuilding while the plane is flying: Sales teams are hitting quota with current (broken) systems. Every change you make risks disrupting their workflow. You'll get pushback on new processes even when they're objectively better.

• Technical debt cleanup: You're inheriting years of band-aid solutions, duplicate records, inconsistent data entry, and undocumented workflows. Before you can build new stuff, you have to fix old stuff. This is unglamorous work.

• Player-coach tension: You need to be strategic enough for C-suite conversations but technical enough to actually configure Salesforce flows. You'll context-switch constantly between architecture discussions and hands-on implementation. If you only want to do strategy or only want to be tactical, this will frustrate you.

• Stakeholder alignment: Everyone has opinions on how systems should work. Sales wants simplicity, marketing wants attribution, finance wants accuracy, executives want executive dashboards. You're constantly negotiating priorities.

What Success Looks Like

• You ship a modernized CRM infrastructure that sales teams actually use without constant workarounds
• Pipeline data is clean enough that forecasting is reliable and leadership trusts the numbers
• Manual processes are automated - things that took 3 people can now run with 1
• You've implemented 2-3 AI-powered workflows that measurably improve conversion rates or reduce manual work

Who You're Supporting

Primary Stakeholders:

• Chief Revenue Officer / Chief Customer Officer
• VP Sales or Head of Membership Growth
• Marketing Operations leadership
• CFO / Finance (for revenue reporting)

What They Care About:

• Clean, reliable pipeline data for forecasting
• Systems that don't break or slow down sales teams
• Automation that scales without adding headcount
• Clear ROI on technology investments

Requirements

• 8+ years in revenue operations, sales operations, or GTM systems roles
• Deep Salesforce expertise - you can build complex flows, validation rules, and custom objects yourself
• Experience with modern GTM stack (enrichment tools, sales engagement platforms, revenue intelligence tools)
• Track record of successful system migrations or large-scale CRM rebuilds
• Comfortable with both strategic planning and hands-on implementation
• Ability to partner with C-suite while also doing technical work
• Understanding of membership/subscription business models (not traditional SaaS sales)
• NYC-based with ability to work hybrid in office