Note: The job is a remote job and is open to candidates in USA. OpenSesame is transforming workforce development with an AI-powered marketplace of skill-building courses and learning pathways. The Sales Operations Manager, Direct Sales is a manager-level individual contributor who partners with Sales and cross-functional teams to improve pipeline management, forecasting, sales processes, tool adoption, automation, territory planning, and operational predictability.
Responsibilities
- Build a deep understanding of the Direct Sales motion, including lead flow, opportunity management, pipeline creation, forecast cadence, sales stages, handoffs, and performance drivers
- Establish strong relationships with Sales leadership, frontline managers, SDR Ops, Enablement, Finance, Marketing, Business Systems, and Analytics
- Audit lead and opportunity management processes to identify gaps in adoption, stage integrity, forecast visibility, seller efficiency, and manager accountability
- Assess pipeline health, CRM hygiene, forecast accuracy, close-date discipline, territory design, quota coverage, and seller tool adoption
- Identify the highest-impact opportunities to reduce seller friction through process simplification, automation, AI-enabled workflows, or better reporting
- Deliver a current-state assessment with prioritized recommendations, including quick wins and longer-term improvements
- Refine lead and opportunity workflows to improve pipeline quality, accountability, and forecast reliability
- Implement pipeline hygiene standards, including stage criteria, aging thresholds, next-step expectations, close-date discipline, and forecast category guidance
- Establish a consistent pipeline inspection and forecasting cadence with Sales leadership and frontline managers
- Build manager-owned operating rhythms so Sales Ops enables accountability without becoming the long-term owner of seller follow-up
- Deliver actionable insights on funnel conversion, sales velocity, win rates, stage progression, deal quality, and rep/segment performance
- Scope automation or AI-enabled opportunities that reduce manual work, improve data quality, or surface risk faster
- Partner with Business Systems and Enablement to support CRM/workflow improvements, rollout readiness, seller communication, and adoption
- Own ongoing pipeline health, stage integrity, forecast inspection, and adoption standards across the Direct Sales motion
- Improve forecast confidence by identifying risk early and surfacing root causes tied to process, coverage, deal quality, seller behavior, or market dynamics
- Establish durable reporting and inspection views for sellers, managers, Sales leadership, Finance, and RevOps
- Assess territory, quota, capacity, and account coverage models; provide recommendations aligned to growth plans
- Surface repeatable insights on ICP fit, account prioritization, deal quality, source performance, and conversion drivers
- Build feedback loops with Marketing, SDR Ops, Partners, Product, Enablement, and CS based on field data and funnel performance
- Drive measurable improvements in tool adoption, seller efficiency, sales cycle visibility, pipeline quality, and forecast accuracy
- Be viewed by Sales leadership as a trusted operating partner who brings clarity, urgency, and practical solutions
- Own pipeline health, stage integrity, and inspection frameworks across the Direct Sales motion
- Lead or support weekly forecasting cadence with Sales leadership and frontline managers
- Pressure-test forecast assumptions using stage progression, deal aging, close-date movement, next steps, source quality, ICP fit, and historical conversion
- Identify forecast risk early and surface root causes tied to process, coverage, deal quality, seller behavior, or market dynamics
- Diagnose seller friction across CRM workflows, sales tools, lead/opportunity processes, and handoffs
- Build scalable processes that improve seller productivity without creating unnecessary administrative burden
- Drive adoption of core sales tools and processes through stakeholder alignment, enablement, manager reinforcement, and adoption tracking
- Partner with Enablement to create clear, practical training and reinforcement materials
- Identify opportunities to use automation and AI-enabled workflows to reduce manual work, improve data quality, and surface insights faster
- Partner with Business Systems, Analytics, and Enablement to scope, test, and roll out workflows that improve seller and manager productivity
- Explore use cases such as CRM update support, call/note summarization, pipeline risk detection, qualification validation, account prioritization, manager inspection summaries, executive forecast summaries, and seller prep automation
- Measure whether automation and AI-enabled workflows improve adoption, efficiency, pipeline quality, forecast confidence, or sales cycle performance
- Design, maintain, and recommend improvements to territory and account assignment models
- Partner with Sales leadership, Finance, Analytics, and SDR Ops on quota modeling, capacity planning, and coverage analysis
- Evaluate account potential, whitespace, greenspace, ICP fit, historical performance, pipeline coverage, rep capacity, and segment dynamics
- Support quarterly and annual planning through scenario modeling and data-backed recommendations
- Analyze sales cycle, conversion rates, win rates, velocity, source performance, and deal quality by segment, source, territory, and rep cohort
- Diagnose performance gaps rooted in process, ICP fit, coverage, source quality, handoff quality, or deal execution patterns
- Translate complex data into clear recommendations for Sales leadership and cross-functional partners
- Build executive-ready narratives that explain what happened, why it happened, what is at risk, and what action should be taken
- Serve as the business owner for Direct Sales process requirements while partnering with Business Systems on technical configuration and implementation
- Translate field needs into clear business requirements
- Support UAT, rollout readiness, seller communication, and post-launch adoption tracking
- Ensure systems changes are practical, scalable, and aligned to how sellers and managers actually work
Skills
- We're looking for proven examples from your career that show you can do this job — that you've built systems, driven alignment, and created impact at scale
- We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire
- All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days
- This position can be based anywhere in the US
- We operate as a remote-first company, and invest in mandatory all-company meetings several times a year in addition to required team travel as necessary
Benefits
- Comprehensive benefits package available to employees upon hire, including ISOs, health insurance, 401(k) matching, and paid time off.
- Comprehensive medical, dental, and vision coverage
- Flexible PTO
- 401(k) matching
- Incentive stock options
- Volunteer time off
- Employee Resource Groups
- A generous professional development program with dedicated annual time off for learning and growth
- Remote-first company
- Hands-on training and clear guardrails to experiment responsibly with AI tools
Company Overview