Head of Revenue Operations
Head of Revenue Operations Parabolic Auto | Chicago, IL | Full-time
Parabolic Auto is modernizing one of the last analog industries in consumer finance. We partner with car dealerships to deliver smarter F&I and aftermarket solutions — making car ownership more affordable for everyday buyers through flexible, transparent payment options. We're a venture-backed SaaS startup moving fast, and we're building the infrastructure that the auto industry has needed for decades.
Every consumer dollar we generate flows through a chain of systems: DMS data comes in, gets scored and routed, dials go out through our contact center, agents work leads with the help of tooling we build, texts and emails follow up automatically, and all of it rolls up into a pipeline marketing and sales live and die by. Today that chain is stitched together by a handful of people wearing too many hats. This role exists to own it end to end.
You'll sit at the intersection of sales, marketing, and analytics — not as a coordinator between them, but as the person who owns the systems and the numbers that make all three functions work together. You'll have your hands on Five9, our dialer and lead routing logic, SalesMSG, the revenue-relevant parts of HubSpot and our CRM stack, and the experimentation process that touches both what consumers see and what our sales team uses. For the right person, this role can also own analytics outright rather than just partnering with it.
This is a build-and-run role, not a steady-state operations role. You'll either build directly (SQL, light scripting, workflow automation, tool configuration) or work closely enough with engineering and product to translate what revenue needs into what gets shipped. We're a small, fast-moving team — you'll have real autonomy, real ownership over the numbers, and the chance to build the revenue operations function from the ground up rather than inherit one.
1. Communications & Contact Center Systems
● Own our telephony and dialer stack (Five9), including campaign configuration, dialer automation, and agent workflows
● Own lead assignment, lead scoring, and lead routing logic across the funnel — from DMS-sourced data intake through to agent queue
● Own SalesMSG and other outbound messaging systems, including sequencing and coordination with call center cadence
● Own the revenue-relevant parts of HubSpot and other CRM tooling — pipeline stages, automation, data hygiene, and reporting structure
● Serve as the primary point of contact for evaluating, implementing, and integrating new revenue tooling as we scale
2. Sales & Marketing Systems Alignment
● Partner closely with sales leadership and marketing to ensure lead flow, attribution, and handoffs work seamlessly across systems
● Build and maintain the reporting infrastructure that gives sales and marketing a shared, trusted view of pipeline, conversion, and funnel performance
● Identify and eliminate friction points in the systems connecting marketing spend to sales outcomes
3. Experimentation
● Own the experimentation process across both consumer-facing initiatives (offers, messaging, channel mix) and sales tooling/workflow changes (scripts, routing logic, dialer strategy)
● Design tests with clear hypotheses and success metrics, and build the infrastructure needed to run and read them reliably
● Turn experiment results into concrete changes to systems, scripts, or routing logic — and track the impact
4. Analytics (Full Ownership for the Right Candidate)
● Partner with or own the analytics function depending on fit: building and maintaining dashboards and reporting that give the company visibility into funnel performance, unit economics, and revenue-driving metrics
● Ensure data flowing from DMS sources, the dialer, CRM, and messaging systems is clean, consistent, and usable for decision-making
● Build the analytical foundation needed to support experimentation and revenue economics decisions
5. Engineering & Product Interface
● Either build automation and integrations directly, or work closely with engineering/product to scope and prioritize revenue systems work
● Translate revenue operations needs (routing logic, scoring models, tooling gaps) into requirements engineering can build against
● Serve as the voice of revenue-facing systems in product/engineering prioritization conversations
6. Revenue Economics
● Act as a key stakeholder in the P&L tied to revenue operations — contact center cost structure, tooling spend, and the efficiency metrics that connect systems investment to revenue outcomes
● Bring a cost-conscious, ROI-driven lens to tooling and systems decisions, and heavily influence how that spend gets prioritized
7. General Revenue Operations
● Identify and take ownership of other revenue operations functions as they emerge — this list isn't exhaustive, and the role is expected to grow with the company
● Build scalable processes and documentation so revenue systems don't depend on founder involvement to run day to day
● 5+ years in revenue operations, sales operations, or a similar systems-and-analytics-heavy role, ideally at a venture-backed startup or high-growth company
● Direct hands-on experience with contact center / telephony platforms (Five9 or similar), CRM systems (HubSpot or similar), and outbound messaging tooling
● Strong analytical skills — comfortable in SQL and/or building dashboards and reporting from scratch; analytics ownership experience is a strong plus
● Experience designing and running experiments across sales and/or marketing systems, with a rigorous, metrics-driven approach
● Comfortable working closely with engineering and product, whether building directly or scoping work for others to build
● Comfort operating with a strong view on unit economics and cost/ROI trade-offs, even without formal P&L ownership
● Demonstrated ability to operate without a large support team and build processes from scratch