Director of Revenue Operations

Director of Revenue Operations

Perry Weather is seeking a Director of Revenue Operations who is equal parts strategic thinker and systems builder. This role sits at the intersection of revenue strategy and operational execution—you'll own our GTM infrastructure, but you'll also drive the strategic initiatives that unlock new markets, improve customer outcomes, and accelerate growth.

You'll have the autonomy to identify problems, architect solutions, and execute with minimal approval layers. You'll partner with sales leadership on go-to-market strategy (market segmentation, pricing strategy, sales motion design), then translate those strategies into scalable systems and processes. You're comfortable in both the board room and debugging data pipelines.

The ideal candidate brings experience scaling revenue operations at fast-growing companies, deep expertise in quote-to-cash and GTM systems, and a proven ability to think strategically about business problems while also executing tactically on the systems that enable them.

Key Responsibilities

• Own revenue operations strategy and execution: Partner with the revenue leadership team to define GTM strategy (market segmentation, customer tiering, sales motion design, pricing strategy), then architect the systems and processes that operationalize that strategy
• Design and optimize our quote-to-cash ecosystem: Own the strategic design and technical architecture of our quoting, order management, and revenue recognition systems across HubSpot, and downstream tools—not just select tools, but architect how they work together
• Drive market and customer segmentation: Lead the data strategy and system design that enables us to segment customers and prospects with precision including tiering, ICP criteria, buying signals, fiscal calendars, budget cycles. Build the infrastructure that lets our sales team walk in Monday morning knowing exactly who to target and why
• Identify and solve operational bottlenecks: As we scale 80-100% YoY and expand into new verticals, continuously identify which systems, processes, and data flows are limiting our growth and architect solutions before they become crises
• Partner with engineering on technical initiatives: Work closely with developers on complex integrations, data pipeline architecture, and system design. Translate business and go-to-market strategy into technical requirements
• Own data quality and integrity: Map complex data flows across systems, identify discrepancies between systems and design pragmatic approaches to clean data while enabling business operations. Ensure downstream systems (customer activation tracking, renewal management, market insights) have reliable data
• Enable revenue visibility and forecasting: Design systems and processes that give leadership accurate, actionable visibility into pipeline, revenue, and GTM performance—not vanity dashboards, but operational intelligence that informs strategic decisions

What Success Looks Like

• You've worked in fast-growing B2B SaaS companies (60-100% YoY growth) where you scaled revenue operations across multiple markets/segments
• You understand both go-to-market strategy (ICP definition, segmentation, sales motion, pricing) and the systems/processes that operationalize it
• You've built or redesigned quote-to-cash systems and can articulate trade-offs between different tools
• You've tackled complex data challenges—consolidating data from multiple sources, dealing with bad migrations, designing systems that work with imperfect data
• You've partnered with engineering teams on non-trivial integrations and can translate business problems into technical specifications
• You can zoom in on tactical details (what fields does this form need?) and zoom out to strategic questions (how do we price our new product tier?) in the same conversation
• You take ownership—you identify problems without being asked and have the confidence to propose solutions and iterate

Why This Matters at Perry Weather:

Perry Weather is at an inflection point. We're growing 80-100% YoY, but we're hitting complexity at scale: multiple verticals with different buying dynamics (education, construction, emerging markets), a hardware + software product with complex quoting and activation challenges, and rapid geographic expansion.

We just raised Series B funding and are implementing a new ERP. Our current systems are creaking under the load of growth, and our data is fragmented across Zoho (hardware), HubSpot (CRM), and other tools. More importantly, we're facing strategic questions that operations must solve: How do we segment customers and markets with precision? How do we improve our education market (our core, now declining) while scaling construction? How do we solve customer activation bottlenecks that directly impact retention?

This role is not a HubSpot administrator or dashboard builder. You'll have the autonomy to make fast decisions, build systems that directly enable our growth, and see the measurable impact of your work on company velocity, revenue, and scalability.

Benefits

• You'll actually want to come in. Our Oak Lawn office isn't just a place to sit, it's where ideas move fast and culture stays strong. The whole team is here Monday through Friday, which means real collaboration, no chasing people down over Slack, and a genuinely fun place to spend your work days.
• Your wellbeing is covered. Competitive health insurance, 401(k) with employer matching, and a full suite of voluntary benefits, because you shouldn't have to think twice about the basics.
• Good people, good times. Monthly All-Hands, Office Olympics, happy hours, and more. We take the work seriously and the culture seriously too.
• You're getting in early, and that matters. We're growing fast, but the biggest opportunities are still ahead. The people joining now will help shape what Perry Weather becomes.