Sales Operations Manager, Direct Sales

About OpenSesame

OpenSesame is transforming workforce development with an AI-powered marketplace of skill-building courses and learning pathways. We help organizations build skills and stay compliant through a high-quality content catalog, seamless LMS/LXP integrations, and advanced capabilities like skills-based curation and multilingual content creation. More than 2,000 companies, including 150+ of the Global 2000, rely on OpenSesame to develop the world's most productive and admired workforces.

About the Revenue Operations Team

The OpenSesame Revenue Operations team is the operational backbone and growth catalyst of the company, enabling our Go-To-Market teams to sell, serve, and scale with clarity and confidence. We design the systems, processes, and insights that turn strategy into execution and ensure revenue flows efficiently from first conversation to renewal.

We partner closely with Sales, Marketing, Customer Success, Partners, Finance, and Legal to remove friction, enforce smart governance, and create a consistent, high-quality customer experience. Our work blends data, process, technology, and judgment to help the business move faster, without cutting corners.

What makes our Revenue Operations team unique:

We embrace automation and AI to reduce manual work, surface insights faster, and scale best practices. We invest deeply in operational excellence and continuous improvement, balancing speed with discipline. We are systems thinkers and problem solvers, motivated by making complex processes simpler and more scalable. We measure success by business outcomes: deal velocity, forecast accuracy, won revenue and customer experience. We operate with an owner’s mindset, taking accountability for results, not just activity. We do the right thing, even when it requires tough conversations or slowing down a deal to protect the business. We communicate with clarity and credibility, serving as trusted advisors to GTM teams and leadership. We believe the best results come from tight collaboration and shared learning, supporting one another through peer problem-solving, documentation, and knowledge-sharing so the entire organization gets better together.

About the Sales Operations Manager, Direct Sales role:

The Sales Operations Manager, Direct Sales is the operational partner responsible for helping the AE organization generate revenue with greater clarity, discipline, speed, and predictability.

This is a manager-level individual contributor role with no direct reports. The role partners closely with Sales leadership, Revenue Operations, Enablement, Finance, Business Systems, SDR, and Marketing to improve how the Direct Sales motion runs from lead and opportunity management through Closed Won.

This is not a reporting-only role or a tactical support desk. The right person will diagnose what is slowing sellers down, pressure-test pipeline and forecast assumptions, identify where process or data is breaking down, and lead operational changes that improve sales execution.

Success in this role means Sales leaders trust the forecast, managers have clear operating views, sellers understand what good looks like, and the business can see where the pipeline is healthy, where risk exists, and where to focus next.

Performance Objectives

Establish Clarity and Trust (First 30 Days)

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.

Build Operational Rigor (60 Days)

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.

Scale Predictability and Impact (90+ Days)

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.

Ongoing Responsibilities

Pipeline, Forecasting & Deal Inspection

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.

Sales Process, Tool Adoption & Change Management

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.

Automation, AI & Seller Efficiency

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.

Territory, Quota, Capacity & Account Strategy

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.

Performance & Funnel Analytics

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.

Business Systems Partnership

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.

You might notice we don’t have the typical list of requirements and buzzwords here. That’s intentional.

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. When you look back a year from now, you’ll know you’ve made OpenSesame better, faster, and stronger because of your leadership.

Although it should go without saying (but it doesn’t), OpenSesame is an equal opportunity employer and we strive to create a welcoming, inclusive environment that celebrates diversity.

We use AI. For real. Every team at OpenSesame works with AI tools daily, not as a buzzword, but as practice. You'll build fluency that most companies are still talking about adopting, with hands-on training and clear guardrails to experiment responsibly. AI amplifies your creativity and judgment. It doesn't replace them. The skills you build here travel with you.

Location: 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.

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences. 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.

Compensation : On-target earnings for this role range between $135,000 and $150,000 per year, depending on experience, which includes base salary and variable incentive compensation based on performance. At OpenSesame, we offer a comprehensive benefits package to employees upon hire, including ISOs, health insurance, 401(k) matching, and paid time off. We carefully consider a wide range of compensation factors, relying on market data to determine compensation and consider your specific job family, background, skills, and experience.

Benefits: Benefits include comprehensive medical, dental, and vision coverage, flexible PTO, 401(k) matching, incentive stock options, volunteer time off, Employee Resource Groups, and a generous professional development program with dedicated annual time off for learning and growth.

Equal Employment Opportunity : OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process.

Pay Transparency : At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website.