[Remote] Sales Operations Manager, Direct Sales

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