Director of Sales Operations

The Director of Sales Operations is a senior leader responsible for architecting, scaling, and optimizing the systems, processes, and insights that power Roo’s revenue engine. This role oversees the full Sales Operations strategy, partnering closely with Growth, Data, Finance, and Marketplace leadership to ensure predictable forecasting, high-quality data infrastructure, and strong cross-functional alignment across all marketplace teams.

This leader owns sales compensation design, HubSpot governance and automation, sales forecasting, market-level performance analytics, and the operational frameworks that support both day-to-day execution and long-term strategic planning. They will build and lead a high-performing Sales Ops team while driving operational rigor, data accuracy, and consistency across our revenue motions.

The Director of Sales Operations plays a critical role in enabling scalable growth for the business, ensuring the systems and insights underpinning our sales engine are robust, efficient, and aligned to company objectives.

• Build and own the long-term Sales Operations strategy aligned to Roo’s revenue growth, GTM model, and marketplace dynamics.
• Establish scalable processes, standards, and systems across supply and demand-facing teams.
• Serve as the primary operational thought partner for the CRO, SVP Marketplace and management team.
• Define and manage the roadmap for CRM architecture, automation, and workflow optimization (HubSpot).
• Drive operational readiness for monitoring supply/demand, product initiatives, and GTM expansions.

• Oversee all forecasting activities in partnership with Finance and Data.
• Implement multi-level forecasting (bottom-up, top-down, weighted pipeline, trend-based).
• Develop dashboards and reporting structures to support monthly pipeline reviews and KPI tracking.
• Establish clear methodologies for pipeline hygiene, data integrity, and forecasting accuracy.

• Own end-to-end compensation design, governance, and quarterly/annual comp planning.
• Develop scalable, transparent commission structures aligned with revenue goals and market conditions.
• Oversee quota setting, territory design, rep capacity modeling, and incentive administration.
• Partner with People Ops and Finance to ensure compliant and timely payouts.

• Partner deeply with Finance, Data and Growth teams to ensure strong data integrity and actionable insights.
• Collaborate with marketing and BD leadership on end-to-end lead management, routing, and funnel optimization.
• Create aligned SOPs between Sales, Marketing, Growth, and Customer Success.
• Support cross-functional strategic initiatives, including OKR planning and cross-team capacity modeling.

• Own HubSpot configuration, governance, and optimization as the system of record for sales.
• Drive automation across reporting, lead management, account health, and performance metrics.
• Evaluate, implement, and integrate additional sales tech stack tools as needed.
• Ensure high adoption and enablement through structured training and documentation.

• Lead, mentor, and develop a high-performing Sales Ops team (including managers and ICs).
• Establish clear KPIs, operating cadences, and accountability mechanisms.
• Foster a culture of continuous improvement, operational rigor, and data-driven decision making.

Required

• 10+ years in Sales Operations, Revenue Operations, or Sales Strategy roles, with at least 5 years leading teams.
• Experience in B2B SaaS, marketplace, or startup environments where GTM motion, CAC/LTV, and field strategy are critical.
• Expert-level knowledge of HubSpot CRM design, sales automation, reporting, and lifecycle configuration.
• Deep experience owning sales forecasting, pipeline management frameworks, and revenue predictability.
• Demonstrated success designing sales compensation plans, quotas, and performance incentive systems.
• Strong experience collaborating with Data and Finance teams on reporting, ETL/data source issues, attribution, and forecasting.
• Ability to set vision and drive from strategy to execution in ambiguous, fast-moving environments.
• Exceptional analytical problem solving with mastery of spreadsheets, dashboards, and data interpretation.
• Excellent written and verbal communication skills with the ability to influence executive stakeholders.

Preferred

• Experience scaling Sales Ops teams from early stage to growth phase.
• Experience in online marketplaces or multi-sided platforms.
• Familiarity with field operations, capacity planning, and GTM design across both supply & demand motions.
• Experience with advanced forecasting models or RevOps tools (Clay, BoostUp, Gong, etc.).

• Predictable, consistent forecasting accuracy across all revenue teams.
• Highly optimized HubSpot architecture with strong adoption and data hygiene.
• Clear, scalable processes for the full sales lifecycle, from lead capture to retention.
• A confident, aligned partnership between Sales Ops, Growth, Data, Finance, and Marketplace leadership.
• A strong Sales Ops team executing against an evolving roadmap with clarity and accountability.

• Every frontline seller and AM can log into HubSpot and immediately see an accurate, prioritized task list, based on SLAs, pipeline stage, account health, and market maturity.
• Adoption >90% and demonstrated improvements in follow-through (task completion, outreach cadences, etc.)

• Standardized dashboards and forecasting models for each active market (supply, demand, conversion, pricing signals).
• This model becomes the single source of truth for CRO, Growth, and Data (this can be negotiated with Albert)

• End-to-end funnel architecture redesigned and automated in HubSpot.
• Clear SLAs defined and automatically enforced (alerts, escalations, task creation).
• Demonstrable improvement in lead response times and conversion rates.

• All comp plans redesigned using best-practice models.
• Quarterly payouts occur with no escalations and <2% adjustment rate.
• Reps report high clarity around how they earn, and Finance validates predictability in commission accruals via eNPS and quarterly people team surveys

• Team delivers consistent forecast accuracy within an agreed margin.
• Forecasting moves from reactive to trend-driven: supply/demand forecasts, AM book growth, pipeline forecasts, territory-level projections.

• Key CRM fields standardized, deduplication automated and consistent.
• Data quality SLAs with Data Team partnership.
• Data team validates that Sales Ops governance materially reduces errors in downstream reporting.

• Lifecycle, automation, scoring, and workflows modernized to support 2–3x volume without manual intervention.
• Clear documentation and training in place so new hires reach competency faster.
• Improved Sales Enablement tools deployed.

• Ops and product workflows built to reduce drop-off.
• Supply churn down quarter-over-quarter.
• Clear, atomic drivers of supply retention identified and built into dashboards and AM tasks.

• A clear internal promotion path for Sales Ops ICs and managers (especially Jesse).
• Evidence of increased autonomy and decision-making across the team.

While we are a remote first company, if you are based in San Francisco this will be a hybrid role.