Dealerware

Revenue Operations

• 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.
• 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.
• 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.

Director, Revenue Operations

Product Manager

• Define how external systems connect to Dealerware and function within the core product.
• Define repeatable API patterns for DMS, scheduling, CRM, and OEM systems. Set clear boundaries and data contracts. Keep decision logic and workflow control inside Dealerware.
• Evaluate and structure third-party integrations to expand capabilities. Retain control over workflow design, user experience, and revenue/pricing models. Limit pass-through integrations and support them only when strategically required.
• Assess trade-offs based on long-term control, margin impact, and reuse across customers. Align decisions with product architecture and roadmap priorities.
• Define how external capabilities are embedded into Dealerware in ways that preserve proprietary logic, protect margin, and increase long-term enterprise value. Ensure integration decisions expand internal IP rather than create vendor dependency.

Senior Product Manager – Strategic Integrations

Account Executive

• Drive new business growth by acquiring new dealerships and dealer groups, expanding revenue, and achieving sales targets.
• Develop and execute territory sales plans to identify and convert high-potential prospects.
• Leverage the MEDDIC sales methodology to qualify leads, structure deals, and close business efficiently.
• Conduct compelling product demonstrations that showcase Dealerware’s impact on dealership operations and profitability.
• Build long-term, trusted relationships with key decision-makers at dealerships, dealer groups, and OEMs.
• Oversee contract negotiations to align on pricing, terms, and long-term success metrics.
• Collaborate with internal teams to refine regional sales strategies and drive product adoption.
• Maintain accurate pipeline tracking, sales forecasting, and CRM data management in Salesforce.
• Serve as the voice of the customer, providing valuable feedback to influence product development and company strategy.

Regional Account Director

Product Designer

• Lead design across the full product development lifecycle, from discovery and concept definition through launch and iteration.
• Immerse yourself in the real work by standing shoulder to shoulder with dealership teams in the service lane, identifying the friction that prevents them from doing their best work, and designing systems that help them show up as everyday heroes for their customers.
• Design end-to-end service experiences, obsessing over every touchpoint across the customer lifecycle, including signup, onboarding, daily use, expansion, and new product adoption.
• Design intelligent, AI-assisted workflows that reduce manual work, increase clarity, and build trust.
• Use modern AI tooling such as Figma Make, Lovable, Cursor, and LLM copilots to accelerate exploration and prototyping while maintaining strong judgment and critical thinking.
• Think in service systems by mapping journeys, states, roles, permissions, compliance logic, and edge cases across onboarding, contracting, daily operations, and expansion.
• Thrive in divergent thinking before converging by exploring broadly, stress-testing assumptions, and narrowing based on real signal.
• Facilitate high-impact workshops and design sessions, pulling from your toolkit (journey mapping, service blueprints, systems mapping, rapid prototyping) to align stakeholders around the right problem to solve.

Senior Product Designer

• Own Dealerware’s web and mobile platform, designing the scalable infrastructure and intelligent workflows that power scheduling, customer verification, mobile check-in, contract execution, and fleet optimization.
• Evolve the core systems that govern the contract lifecycle, ensuring configurability across OEM programs.
• Shape the mobile platform into the heartbeat of daily dealership operations with modern, intuitive experiences.
• Embed AI and automation directly into core scheduling, contracting, and customer profile workflows.
• Define and instrument platform KPIs tied to dealership economics, ensuring the platform acts as a multiplier across the ecosystem.
• Operate with high ownership across Engineering, Product Design, Data, and GTM to ensure platform investments are scalable and economically meaningful.

Senior Product Manager – Platform

• Responsible for building and scaling Dealerware’s intelligence product line
• Transform fleet data into monetizable intelligence embedded into the platform
• Identify economically material problems within fleet operations
• Define analytical frameworks required to solve them
• Report on the product roadmap, enterprise and OEM requirements
• Develop monetizable analytics capabilities tied to customer impact

Senior Product Manager – Insights, Advanced Analytics

• Partner with the VP of Data Engineering to drive a company-wide, insight-driven mindset.
• Define a product vision that evolves Dealerware from reporting → insights → intelligence.
• Develop pricing and packaging strategies that monetize insights by delivering clear, outcome-driven value to customers.
• Lead the end-to-end lifecycle of insights and analytics products—from ideation and discovery to launch and iteration.
• Translate complex datasets into intuitive dashboards, workflows, and intelligence surfaces that customers actually use.
• Ensure high standards for accuracy, usability, and adoption—not just delivery.
• Engage directly with dealerships, dealer groups, and OEMs through discovery calls, on-site visits, and ongoing research.
• Identify jobs-to-be-done and decision points where insights can materially change outcomes.
• Post-launch, measure adoption and impact, and partner with Customer Success, Sales, and Marketing to drive sustained usage.
• Design reporting and insights that support accounting workflows, compliance needs, and operational decision-making.
• Balance financial rigor with usability for non-technical users.
• Collaborate with engineering, design, marketing, sales, customer success, and partnerships.
• Influence without authority, aligning teams around a shared insights vision.
• Track competitive and industry trends in automotive analytics, AI, and fleet intelligence.
• Identify opportunities to apply AI/ML (predictive analytics, natural language summaries, anomaly detection, automation) to customer problems.
• Champion experimentation that moves Dealerware ahead of traditional BI and static reporting.
• Balance ambition with pragmatism—shipping value early and often.
• Rally teams around your vision and create momentum across the organization.
• Navigate trade-offs thoughtfully, always looking for win-win outcomes.