Sales Development Manager - OpenSesame

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 productive and admired workforces.

About the Role

OpenSesame is entering a new phase of growth — evolving from a product-led to a multi-product, AI-enhanced SaaS company. The Sales Development (SDR) team sits at the forefront of this transformation. As our Sales Development Manager, you will lead the team that fuels our outbound pipeline, engages in meaningful conversations with L&D and HR leaders, and sets the standard for modern, human-centered, AI-powered outbound sales.

Reporting to the Director of GTM Operations, this role balances strategy and execution. You will build an SDR function that leverages modern AI tools to enhance research, messaging, and timely coaching, while keeping the human touch at the heart of every interaction. You will collaborate closely with Marketing, Partners, Sales, Enablement, and RevOps to drive pipeline growth, process consistency, and professional development.

Performance Objectives

First 30 Days - Orientation & Assessment

• Build a foundational understanding of OpenSesame’s go-to-market strategy, ideal customer profiles, and competitive landscape.
• Audit existing SDR processes, messaging, and cadences across Gong Engage, Salesforce, and ZoomInfo.
• Assess SDR performance metrics (activity → meeting, meeting → opportunity, velocity) and identify key bottlenecks.
• Conduct 1:1s with every SDR, AE, and cross-functional partner to understand strengths, challenges, and development goals.
• Deliver a baseline performance report and outline 2–3 high-impact quick wins to drive immediate improvement.
• Outline an execution plan for automated inbound management.

By 60 Days - Optimization & Team Enablement

• Launch the first version of the AI-Enhanced Outbound Playbook, integrating tools like Gong Engage, Qualified, Clay, ZoomInfo, and ChatGPT Enterprise.
• Coach SDRs on balancing automation with authentic outreach, reinforcing engagement and messaging consistency.
• Partner with Marketing to launch 2–3 account-based outbound campaigns targeting key verticals and target account lists.
• Engage with our Partner organization to improve and enhance Partner lead processes.
• Establish a weekly coaching rhythm using Gong analytics, call reviews, and performance dashboards.
• Optimize dashboards tracking inbound and outbound conversion, pipeline creation, and ROI in real time.
• Establish a closed-loop feedback process for capturing seller and sales leader insights.

By 90 Days - Predictable Performance & Team Development

• Drive the SDR team to 100% attainment of monthly qualified opportunity targets.
• Partner with AEs and RevOps to refine qualification criteria and improve lead handoffs.
• Refine account-based outbound campaigns and create quarterly campaign strategy frameworks in partnership with Marketing.
• Introduce a development framework for SDR to AE progression.
• Implement reporting demonstrating SDR impact on pipeline and revenue while analyzing MQL quality.
• Strengthen remote team culture through consistent rituals such as call-of-the-week breakdowns and win shares.

By 180 Days - Scale & Systematize

• Institutionalize a repeatable Outbound Operating System—including training guides, cadences, and KPI dashboards.
• Achieve full team quota attainment (100%+ of sales qualified targets).
• Improve overall outbound conversion rates by 10%+ over baseline.
• Develop and document best practices for AI-assisted prospecting.
• Align outbound campaigns with product launches and thought leadership initiatives.
• Launch seller satisfaction survey framework to capture feedback on SDR performance.

Compensation & Benefits

• Base Salary: $110,000 – $119,000 per year (bonus eligible; OTE ranges from $157,000 to $170,000)
• Equity: Incentive stock options
• Health Coverage: Comprehensive medical, dental, and vision insurance
• Retirement: 401(k) matching
• Time Off: Flexible PTO and volunteer time off
• Growth: Generous professional development program with dedicated annual time off for learning
• Work Environment: Remote-first culture with company offsites (travel required up to 35 days per year for leadership)