Fractional RevOps / GTM Engineer (Part-Time, Contract)

Anagram is the ultimate insurance billing platform for eye care providers. Combining instant eligibility and benefit verifications, patient responsibility calculation, claims management, payment posting, and more, Anagram’s all-in-one revenue cycle management solution is designed to save providers time and money, and free doctors to deliver the best care for their patients. Our mission is to simplify insurance, and it’s working: over 2,000 eye care professionals rely on Anagram to manage their insurance billing. Founded in 2014, Anagram is the largest and fastest-growing insurance billing platform for eye care providers in America and processes hundreds of millions of dollars each year. About the Role We’re looking for a hands-on RevOps/GTM engineer to own the revenue systems layer across a genuinely messy and interesting go-to-market. You’ll design and maintain the pipes connecting CRM, billing, warehouse, and analytics, and wire AI into the workflows in between. You’ll work directly with revenue leadership and have wide latitude in how things get built. Why This Role Is Harder Than It Sounds • The account hierarchy is real. Our market spans solo practices, multi-location companies, roll-up brands, and PE platforms. The HubSpot company object has to do quadruple duty — PE firm → brand → company → location — with clean parent-child associations, dedup logic that respects the hierarchy, and reporting that rolls up correctly at every level. • Four GTM motions run in parallel. SMB, mid-market, enterprise, and partner led — each needs its own routing, lifecycle logic, handoffs, and funnel reporting, without forking the CRM into four incompatible systems. • Three products, three pricing models. Subscription, usage-based, and percentage-of-collections billing all flow through the same revenue stack. Normalizing these into coherent ARR/NRR, cohort, and revenue reporting is a core design problem, not an afterthought. About You • You’re a hands-on RevOps/GTM engineer with a builder profile. • Strong SQL from scratch. • You know when a Zap is enough and when it’s time to write code. • Self-directed; comfortable operating fractionally with async communication and minimal oversight. What We’re Looking For Must-Haves • 4+ years in RevOps, GTM engineering, or sales/marketing ops with a builder profile • Deep, hands-on HubSpot experience custom objects, associations, workflows, API —ideally with complex parent-child account structures (multi-location, franchise, healthcare, or roll-up environments) • Production experience with Stripe data, including usage-based or non-standard billing models • Production experience with Zapier • Practical experience building with Claude or comparable LLM APIs, prompting, evaluation, and knowing the failure modes • Self-directed; comfortable operating fractionally with async communication and minimal oversight Nice-to-Haves • Healthcare or vertical SaaS experience; familiarity with provider data (NPI/NPPES, CMS datasets) • Experience supporting multiple concurrent GTM motions (PLG/SMB velocity alongside enterprise sales) • dbt and enrichment tooling (Apollo) What You’ll Do • CRM architecture (HubSpot): The parent-child company model, lifecycle stages, lead routing by segment, workflows, dedup, and data hygiene. You keep the CRM trustworthy so pipeline numbers are real at both the location and parent level. • Billing-to-CRM sync (Stripe): Reconcile heterogeneous billing data (subscription, usage, % of collections) with CRM records; surface churn, expansion, and payment signals where the revenue team can act on them. • Automation (Zapier + scripting): Build and maintain the integration layer. Know when a Zap is enough and when it’s time to write code. • Data warehouse (Snowflake): Model GTM and revenue data into clean, queryable tables that handle the hierarchy and mixed pricing models. Strong SQL from scratch. • Analytics (Metabase): Dashboards leadership actually uses funnel conversion by motion, pipeline coverage, revenue normalized across pricing models, rollups by parent account. • AI workflows (Claude): Lead enrichment and scoring, call summarization, follow-up drafting, and data cleanup at scale, including provider-level enrichment from industry datasets (NPI/NPPES). Anagram offers employees: • Industry-leading compensation, including salary and equity ownership • MacBook, monitor, and all the technologies you need to succeed • Full Medical & Dental Insurance • Unlimited PTO • 401k • Remote first company • Fast-paced startup environment Anagram is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy), sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by applicable law.