Senior Director, GTM Revenue Operations

The Senior Director, GTM Revenue Operations, is both the strategic and technical backbone of how ChowNow's Sales, Onboarding, and Customer Success teams operate day to day. This is not a reporting-and-dashboards role — it's an operator and systems-architect role. You'll need to understand the GTM motion deeply enough to sit in a rep's or post sales rep’'s shoes, spot exactly where a process is broken or a workflow is creating friction, and then personally architect the fix — not as an isolated patch, but as part of a coherent system that holds up as we scale.

This function exists because of where the business is today: years of incremental, band-aid fixes and one-off customizations have left us with real tech debt across Salesforce, HubSpot, PlanHat, and the tools connecting them. Small changes take too long, and they too often break something else in the process. We need someone who can see the whole board — not just the piece in front of them — untangle what's been glued together, and rebuild it so that future changes are fast, safe, and durable.

You'll lead three key functions: a Sales & CS Business Ops (who lives inside the sales and CS org, diagnosing friction and defining the fix), a Marketing & Partner Ops Manager (who owns the demand and partner tech stack end to end as our HubSpot admin), and a Biz Systems team who build and maintain our core systems. Your job is to make sure these three functions work as one connected system rather than three disconnected ones — translating GTM needs into technical requirements, and technical constraints back into GTM strategy, so nothing gets lost in either direction.

This role reports directly to the CEO and will own a team of 5-7 direct reports.

This is a remote role based in the United States. Please note: ChowNow is not eligible to employ in every state and the recruiting team will confirm location and eligibility before moving past initial stages.

GTM Process & Team Leadership

• Deep, ongoing immersion in how Sales, Onboarding, and CS actually operate — their blockers, their workarounds, and where the real friction lives, partnering closely with the Sales & CS Business Partner to diagnose it

• Turning diagnosed problems into defined solutions: a new workflow, a re-architected process, a system redesign — and owning the decision on what the right fix actually is

• Managing and developing the Sales & CS Business Partner and Marketing & Partner Ops Manager, ensuring their work stays connected rather than siloed

Systems Architecture

• Acting as the systems architect across our GTM stack (Salesforce, HubSpot, PlanHat, Gong, PartnerStack, LeanData, Bookit and adjacent tools) — thinking through the full chain of impact before any change is made, not fixing one system in isolation

• Leading the effort to unwind existing technical debt: legacy customizations, redundant automations, and fragile integrations that make small changes slow and risky

• Setting technical standards and review processes so that new changes are built to scale rather than added as another layer of patchwork

• Directly managing the Biz Systems team, prioritizing their roadmap against both the tactical fixes surfaced by the Business Partner roles and the larger architectural rebuild this function requires

Strategic Operations

• Owning the connective tissue between diagnosis (GTM Strategy & Analytics function), execution on the sales/CS side (Business Partner), and execution on the marketing/partner side (Marketing & Partner Ops) — ensuring a fix identified in one place is implemented consistently everywhere it touches

• Territory and compensation planning infrastructure, forecasting rigor, and cross-functional alignment on how GTM processes are designed and rolled out

• Advising CEO on where the biggest process and systems risks or opportunities are, with a point of view on sequencing and tradeoffs

• Have 8+ years of Revenue Operations experience in a SaaS environment, including meaningful time in a hands-on systems/technical capacity — not purely a reporting or analytics background

• Have 5+ years managing a team across RevOps, MarOps, CS Ops and Business Systems (SalesForce)

• Have deep, practical fluency in Salesforce and HubSpot; experience with PlanHat, Gong, PartnerStack, and LeanData is a strong plus

• Have direct experience untangling legacy systems, customizations, or technical debt — not just building net-new

• Think in systems, not tickets: you naturally trace a proposed fix through everything it touches before committing to a build

• Have a proven track record of translating messy, ambiguous business pain points into a clear technical solution and seeing it through to execution

• Are comfortable being both strategic (advising leadership on sequencing and risk) and deeply in the weeds (reviewing a workflow or automation yourself when needed)

• Have experience partnering with Sales, CS, and Marketing leadership, and can speak credibly to both a rep on the floor and an engineer building the fix

• Have managed compensation, territory, or forecasting infrastructure in a prior role