About the Company:
Highway is the fastest-growing freight tech provider in North America. We serve the largest freight brokers in the industry, solving one of their biggest pain points: who is really hauling their freight. We answer the question of Carrier Identity, protecting brokers’ networks, preventing fraud and increasing transparency. Serving and protecting our customers is our top priority, and we are proud that our best marketing is our customer referrals and testimonials.
Role Description:
We are seeking a strategic and analytical Sales Operations Manager to optimize our sales processes, drive forecasting accuracy, and enable data-driven decision-making across the sales and customer success organizations. This role will serve as the operational backbone of our sales function, ensuring seamless pipeline management, accurate reporting, and cross-functional alignment with Marketing and Customer Success teams.
Your role:
- Build and maintain role-based sales dashboards and reports tracking pipeline health, deal velocity, quota attainment, conversion rates, and rep performance
- Support sales forecast accuracy through historical analysis, pipeline coverage modeling, and predictive analytics
- Conduct win/loss analysis, conversion rate tracking, and sales cycle analysis to identify trends and improvement opportunities
- Provide ad-hoc analytical support to sales leadership for strategic decision-making, territory reviews, and performance evaluations
- Partner with Marketing Operations to document, implement and monitor defined lead definitions (MQL, SQL), SLAs, handoff processes, and attribution methodology; surfacing gaps and recommendations to Sales and Marketing Leadership
- Collaborate with Customer Success on various initiatives, retention campaigns, and expansion plays
- Work closely with Learning & Development to identify training needs, measure training effectiveness, and ensure reps have the tools and knowledge to execute
- Participate in Revenue Operations initiatives to ensure unified go-to-market alignment across business units
- Serve as liaison between Sales and Business Systems for system enhancements, data requests and requirements gathering including the translation of business problems and needs into solutions
- Operationalize and scale standardized sales processes through clear stage definitions, exit criteria, and SLAs across business units
- Establish and enforce data governance policies to maintain CRM data integrity and pipeline hygiene across multiple business units
- Partner with Sales Leadership to operationalize sales methodologies (MEDDIC, Challenger, Sandler) through CRM processes, business systems and process playbooks
- Track key sales metrics (new bookings, ASP, sales cycle length, win rates) and surface insights that enable BU Sales Leaders to coach and drive accountability
- Ensure data flows cleanly across systems through proper configuration, validation rules, and enrichment protocols
- Design and maintain integrations between CRM, ChurnZero, marketing automation, and reporting platforms to eliminate data silos (in collaboration with the Business Systems Administrator)
- Evaluate, recommend, and implement sales operations tools (automation, intelligence, forecasting, analytics platforms)
- Build data pipelines that consolidate sales, customer success, finance, and marketing data into centralized reporting infrastructure
- Collaborate with FP&A on integrated revenue planning, aligning sales forecasts with financial projections and budget assumptions
- Analyze revenue drivers (new business, expansion, churn, pricing) to identify trends, risks, and opportunities
- Support design and optimization of quota structures, compensation plans, and incentive programs
- Conduct monthly and quarterly variance analysis comparing actual results to plan, identifying root causes and recommending corrective actions
Qualifications:
- Bachelor's degree in Business Administration, Finance, Information Systems, or related field
- 3-5+ years of experience in Sales Operations, Revenue Operations, or similar role at a B2B SaaS company
- Proven experience in sales forecasting, territory planning, and quota management at a growing company (ideally $20M-$100M+ ARR stage)
- Demonstrated success implementing sales processes and systems at scale across multiple teams or business units
- Advanced proficiency with CRM platforms (Salesforce or HubSpot), including system administration, workflow automation, and custom object configuration
- Strong Excel/Google Sheets proficiency (pivot tables, VLOOKUP, data modeling, statistical analysis)
- Experience with data visualization and BI tools preferred (Tableau, Looker, Power BI, or similar)
- Familiarity with customer success platforms (ChurnZero, Gainsight, Totango) and renewal forecasting methodologies