What is the role of a Director, Revenue Operations at Dealerware?

The Director, Revenue Operations position at Dealerware is a Full-time or part-time position opportunity in the Executive/Management field.

Where is this Director, Revenue Operations job located?

Kingston (Downtown), Ontario, K7L, Canada

What type of employment is offered for this Director, Revenue Operations role?

Full-time or part-time position

What is the expected salary for this Director, Revenue Operations job?

Compensation will be discussed during the hiring process.

How can I apply for the Director, Revenue Operations position at Dealerware?

You can apply directly through the application link provided.

Director, Revenue Operations at Dealerware

Director, Revenue Operations

About Dealerware

Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. Dealerware is committed to being a people-first culture and a great place to work for all, with flexible scheduling, unlimited PTO, extensive benefits, a core value of Diversity, Equity & Inclusion, and a leadership and management team that defaults to being supportive and accessible. In 2026, Dealerware was recognized by Built In as one of their Best Startups to Work for in Austin for the fifth consecutive year.

We are looking for a strategic, execution-oriented Director, Revenue Operations to join our team. This role is responsible for driving revenue predictability, operating rigor, and cross-functional alignment across Sales, Marketing, Customer Success, and Finance. The Director, Revenue Operations helps design and scale the revenue operating model, owning forecasting, analytics, and performance visibility to ensure leadership has a clear, actionable view into results, risks, and opportunities. Partnering closely with executive leadership, this individual operates at the intersection of data and strategy—shaping how Dealerware scales our go-to-market across OEMs, Dealer Groups, and Dealerships.

As Director, Revenue Operations, you will be responsible for:

Revenue Operating Model & Forecasting Rigor

Define and operationalize Dealerware’s go-to-market operating cadence, including pipeline reviews, forecasting cycles, and executive reporting, creating consistency and accountability across go-to-market teams.
Drive improvements in sales productivity, pipeline health, and sales velocity through disciplined deal inspection, coaching insights, and data-driven recommendations.
Own forecasting methodology, pipeline management, scenario modeling, and variance analysis in partnership with Sales leadership and Finance, improving forecast accuracy and process.
Provide leadership with clear visibility into revenue performance, risk, and upside to support faster, higher-quality decision-making at the board and management level.

GTM Systems, Data, & Process Scale

Own the strategy, optimization, and scalability of the revenue technology stack (CRM, sales engagement, outreach, marketing automation, analytics, etc.).
Design and continuously improve scalable GTM processes across the full customer lifecycle, from pipeline creation through renewal and expansion.
Build and automate workflows that improve efficiency, pipeline hygiene, and predictability as the business scales.
Evaluate, pilot, and scale best-in-class AI technologies across the go-to-market stack to improve team efficiency, demand generation, sales velocity, and pipeline yield.

Cross-Functional Leadership, Insights & Enablement

Align Sales, Marketing, Customer Success, and Finance around shared goals, metrics, definitions, and execution standards.
Translate performance data into actionable insights and recommendations for GTM and executive leadership, influencing strategy, resourcing, and priorities.
Partner with Enablement and GTM leaders to drive adoption of tools, processes, and operating standards.
Lead the Revenue Operations function, supervising a team of 1–2.
Build the team over time, including hiring, developing, and scaling the team to support long-term growth.

Required qualifications:

7+ years of experience in Revenue/Sales/GTM Operations and/or GTM Engineering within growth stage, SaaS companies ($50M–$100M+ ARR).
Proven ownership of CRM systems, revenue analytics, and GTM reporting at scale.
Experience partnering closely with Sales leadership and Finance on forecasting process, planning, and executive reporting.
Strong analytical judgment with the ability to translate data into executive-level insights and recommendations.
Demonstrated track record of influencing cross-functional leaders and driving durable change without direct authority.
Proficiency in Salesforce, Hubspot, and Outreach with experience implementing and scaling best-in-class AI technologies across the go-to-market stack.

Dealerware offers you:

Full benefits (medical, dental, vision, disability)
401(k) with company match
On-demand educational courses via LinkedIn Learning
Tuition reimbursement and continuing education
Unlimited paid vacation policy
Flexible work
Generous Paid Parental Leave program
Modern office and a dynamic team in downtown Austin with free parking
Friendly, small company environment with a progressive culture

Dealerware is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances. Dealerware's management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, access to facilities and programs and general treatment during employment.

*We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.

Director, Revenue Operations at Dealerware – Kingston (Downtown), Ontario

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