Sales Development Manager

About OpenSesame

OpenSesame is the trusted partner for Workforce Reinvention in the age of AI. OpenSesame delivers integrated software, curated and customizable content, and expert services – embedded into existing learning, HR, and work systems – to help organizations expand their human+AI potential and thrive through change.

About the Team

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’ll lead the team that fuels our outbound pipeline, engages in meaningful conversations with L&D and HR leaders, and sets the standard for what modern, human-centered, AI-powered outbound looks like.

About the Role

This role is about more than managing activity. You’ll scale a predictable outbound engine, develop future sales talent, and redefine how OpenSesame connects with the market — through a balance of technology, creativity, and empathy.

You’ll blend strategy and execution, building an SDR function that leverages AI tools to enhance research, messaging and timely coaching, while keeping the human touch at the heart of every interaction. You will work closely with Marketing, Partners, Sales, Enablement and RevOps, to turn insight into action — driving pipeline growth, process consistency, and professional development across the team.

Reporting to the Director of GTM Operations, this is a highly visible leadership role with a direct impact on pipeline, revenue and GTM innovation.

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.

Success by Day 30: Clear SDR performance baseline, planned approach for early optimizations, and a 10+% improvement in activity-to-meeting conversion through data-driven tweaks and workflow efficiency.

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 to automate research, personalization drafts, lead qualification and post-call notes.
• Coach SDRs on balancing automation with authentic outreach, reinforcing high-quality engagement and messaging consistency.
• Partner with Marketing to launch 2–3 account-based outbound campaigns targeting top verticals and / or target account lists.
• Engage with our Partner organization to improve and enhance our Partner lead processes
• Establish a weekly coaching rhythm using Gong analytics, call reviews, and performance dashboards to ensure feedback is timely and impactful.
• Optimize existing dashboards that track inbound and outbound conversion, pipeline creation, and ROI in real time.
• Establish a closed loop feedback process for capturing seller and sales leader insights in order to continuously improve SDR support.

Success by Day 60: SDRs are operating with greater precision and confidence, with 5-7% improvement in meeting-to-opportunity conversion rates, and new playbook adoption exceeding 90%.

By 90 Days - Predicable Performance & Team Development

• Drive the SDR team to 100% attainment of monthly qualified opportunity targets, with top performers achieving full quota.
• Partner with AEs and RevOps to refine qualification criteria and improve lead handoffs.
• Refine account-based outbound campaigns and create campaign strategy framework for upcoming quarter in partnership with Marketing.
• Introduce a development framework for SDR → AE progression, identifying high-potential talent for future roles.
• Implement consistent reporting to the business demonstrating SDR impact on pipeline / revenue while providing analysis on MQL quality to improve Marketing ROI.
• Strengthen remote team culture through consistent rituals — call-of-the-week breakdowns, win shares, and transparent leaderboard recognition.

Success by Day 90: A confident, data-driven SDR team operating with rhythm and accountability, contributing predictable pipeline and demonstrating measurable skill growth.

By 180 Days - Scale & Systematize

• Institutionalize a repeatable Outbound Operating System — including training guides, cadences, and KPI dashboards — to support new hire ramp and predictable team performance.
• Achieve full team quota attainment (100%+ of sales qualified targets).
• Improve overall outbound conversion rates by 10%+ over baseline through targeted messaging, data refinement, and coaching.
• Develop and document best practices for AI-assisted prospecting, ensuring consistency in quality and tone across the team.
• Partner with Marketing to align outbound campaigns with product launches, develop top-of-mind thought leadership and improve campaign strategy.
• Launch seller satisfaction survey framework to capture seller feedback on SDR performance

Success by Day 180: A fully optimized outbound function that blends automation and authenticity, with measurable improvements in pipeline quality, velocity, and conversion efficiency.

Ongoing – Leadership, Growth & Continuous Improvement

• Build a high-performance culture of accountability, curiosity, and career growth with proper incentive plans to support.
• Continuously refine outbound strategies based on performance data and market shifts.
• Promote SDRs into AE or other roles, building a visible talent pipeline across the revenue organization.
• Collaborate cross-functionally to ensure outbound insights shape company-wide targeting and messaging.
• Champion a balance of human connection and AI innovation in everything the team does.

12-Month Success Snapshot:

• SDR team consistently achieving 110% of pipeline creation targets.
• New hires consistently achieve 100% quota by month 3.
• 25–30% improvement in outbound conversion rates year over year.
• A well-documented, scalable outbound system embedded across GTM teams.
• Visible talent progression, with multiple SDR-to-AE promotions.
• A reputation for excellence, creativity, and modern outbound leadership

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.

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.