Director of GTM Strategy and Operations

About the Role

We're looking for a Director of GTM Strategy and Operations to be the operational engine behind our go-to-market team. We know our market — now we need to win it faster. This role is about building the infrastructure, automation, and analytics that compress our sales cycle, increase pipeline velocity, and give leadership the visibility to forecast with confidence.

You'll sit at the intersection of sales operations, marketing operations, and revenue intelligence — owning the systems, data, and workflows that turn our GTM strategy into repeatable, measurable execution. This is not a 'keep the lights on' role. You'll identify gaps, design solutions, and drive adoption across the team.

What You'll Do

Revenue Operations & Automation

• Own and evolve the GTM tech stack — Salesforce, HubSpot, and the surrounding ecosystem — ensuring clean data flow, tight integrations, and minimal manual work
• Design and implement automation across the funnel: lead routing, handoff workflows, enrichment pipelines, follow-up sequences, and deal stage triggers
• Build and maintain integrations between revenue tools (CRM, MAP, sequencing platforms, data enrichment, BI) so teams operate from a single source of truth
• Identify and eliminate process friction that slows deals down — from first touch through closed-won
• Partner with technical resources to architect scalable RevOps infrastructure; you set the strategy and requirements, others execute the builds

Sales Operations & Cycle Optimization

• Operationalize the sales process — MEDDPICC adoption, stage exit criteria, deal inspection frameworks — so reps are consistent and managers have real visibility
• Build and maintain pipeline management cadences: weekly reviews, deal health scoring, and escalation triggers that surface risk early
• Analyze sales cycle data to identify where deals stall, drop, or slow — then build fixes into the process and tooling
• Partner with Sales leadership on territory management, quota modeling, and capacity planning
• Support call review and coaching workflows to surface winning patterns and replicate them across the team

Data, Tracking & Analytics

• Define and own the GTM data model: what we track, how we track it, and how it flows between systems
• Build dashboards and reporting that give leadership real-time visibility into pipeline health, velocity, conversion rates, and forecast accuracy
• Create predictive models and lead/deal scoring frameworks that help reps and managers prioritize where to spend their time
• Establish win/loss tracking and analysis to feed continuous learning back into sales and marketing strategy
• Ensure data hygiene across CRM and marketing platforms — standardized fields, enforced inputs, reliable reporting

Marketing Operations

• Partner with Marketing on campaign attribution, lead lifecycle tracking, and MQL-to-SQL conversion optimization
• Own the lead routing and handoff process between marketing and sales — clean, fast, and accountable
• Build closed-loop reporting between marketing activity and revenue outcomes
• Support segmentation models that power targeted campaigns, personalized outreach, and account prioritization

What We're Looking For

Must-Haves

• 7+ years in revenue operations, sales operations, or GTM strategy at a B2B SaaS company
• Deep hands-on experience with Salesforce and HubSpot — you know how to configure, integrate, and get the most out of both
• Proven track record building automation and workflow systems that measurably improved sales team efficiency or cycle time
• Strong analytical skills — you can build a model, interpret pipeline data, and translate findings into clear recommendations for leadership
• Experience building or owning forecasting and pipeline visibility frameworks
• Excellent communicator who can work across Sales, Marketing, and the C-suite without losing clarity or speed
• A bias toward automation: if you do something twice, you build a system for it
• Comfort with AI/LLM tooling for GTM use cases — you've used it to save time and you'll bring that mindset to the team

Nice-to-Haves

• Experience with enrichment and data tools: Clay, Apollo, Clearbit, ZoomInfo, or similar
• Familiarity with workflow automation platforms like Zapier, n8n, or Make
• Experience with BI/reporting tools (Tableau, Looker, or similar)
• Background in or exposure to the insurance or insurtech space

Why This Role

You'll have direct access to C-level leadership and real ownership over the systems and strategy that drive revenue. This is a build role — we have the foundation, the market, and the product. We need someone who can operationalize it all and make our GTM team run faster and smarter. If you want the seat where those decisions get made, this is it.

90-Day Success Milestones

1. Systems audit and roadmap — document current state of the GTM stack, identify integration gaps, data quality issues, and automation opportunities; deliver a prioritized roadmap
2. Pipeline visibility and forecasting — build or rebuild the dashboards and cadences leadership uses to inspect pipeline health and call the number
3. Quick wins on automation — identify and ship 2–3 high-impact automation improvements (lead routing, handoff workflows, follow-up sequences, or similar)
4. Win/loss framework — design and stand up a structured win/loss program that feeds insights back to sales and marketing on a recurring basis