About The Position

We are seeking an accomplished and results-driven Sales Leader to define and lead the sales strategy at Rustici Software. As part of a strategic growth initiative, you will expand our go-to-market strategy, working directly with the CEO and executive leadership team. This role offers a significant opportunity to establish a new outbound sales channel targeting Enterprise and Midmarket customers, with potential to also target Content Publishers and Associations. You will build and lead the sales engine, leveraging existing inbound sales, account management, and marketing support. Rustici's software products address content and platform interoperability challenges, specializing in standards like SCORM and xAPI to help customers enhance their products and enterprise learning ecosystems. The ideal candidate possesses deep business development and sales expertise, strong knowledge of sales technology, and experience in the learning technology space, particularly with early-stage/growth-stage products. This role requires building and leading a high-performing sales team and developing relationships with C-level executives, HR leaders, and IT decision-makers.

Requirements

  • 8+ years in B2B SaaS sales, with at least 3 years in a VP or Head of Sales role.
  • Demonstrated success building or rebuilding a sales function at a company in the $15M–$100M ARR range.
  • Direct experience selling learning/HR technologies into enterprise — familiarity with the CLO/CHRO/COO/CIO buying dynamic is a significant advantage.
  • Experience selling early-stage/growth-stage products.
  • Experience with both direct enterprise sales (12–18 month cycles) and higher-velocity mid-market motion.
  • Proven track record of consistently meeting/exceeding team sales targets and revenue growth, driving continuous improvement in a sales environment, particularly leveraging of sales technology to improve velocity and efficiency.
  • Strong expertise in business development, from lead generation to closing.
  • Experience creating and executing sales strategies in highly competitive markets.
  • Broad understanding of sales support technology and an expert in leveraging technology & tools to drive sales velocity & efficiency.
  • Can write the playbook and execute it — not just manage people who execute.
  • Rigorous forecasting discipline using leading indicators, not just gut feel.
  • Strong recruiter: knows how to attract A-players.
  • Data fluent: comfortable in CRM (Salesforce preferred), understands funnel metrics, can build a board-ready pipeline report.
  • Clear communicator who can represent the sales org to the board.

Nice To Haves

  • Experience in the learning technology space.
  • Experience selling early-stage/growth-stage products.

Responsibilities

  • Build and own the full sales playbook: outbound motions, discovery frameworks, demo narrative, objection handling, and competitive displacement strategies.
  • Design the channel mix — direct enterprise, mid-market, and partner/reseller — and decide sequencing and investment by segment.
  • Create and execute a comprehensive sales strategy focused on acquiring and expanding enterprise accounts, aligning with company goals and market opportunities.
  • Establish pipeline generation cadences in partnership with marketing.
  • Recruit, hire, onboard, and develop a high-performing sales team that scales based on achieving key milestones.
  • Model the behaviors you want to see — as a Builder, you will be actively involved in key deals and establishing the initial pipeline.
  • Oversee the existing inbound sales team and Account Management teams that are responsible for driving growth from existing markets and accounts.
  • Foster a culture of excellence, collaboration, and continuous improvement.
  • Oversee all sales processes to drive the team’s deal velocity.
  • Represent Rustici as a key stakeholder in key deals where needed to assist in bringing them to a win.
  • Maintain a strong understanding of the Revenue pipeline, provide accurate sales forecasts, and ensure the timely execution of opportunities.
  • Regularly update the executive team on sales progress, opportunities, and roadblocks.
  • Own and deliver the annual revenue number and quarterly forecast with board-level rigor.
  • Instrument the full sales funnel: pipeline coverage ratios, conversion rates, ACV trends, win/loss analysis.
  • Stay ahead of industry trends, competitor offerings, and emerging technologies.
  • Share relevant insights with the product, marketing, and leadership teams to shape the company’s sales and product strategies.
  • Leverage modern sales technologies, CRM tools (Salesforce, HubSpot, etc.), and sales enablement platforms to streamline sales processes, improve forecasting accuracy, and track key performance metrics.
  • Ensure best practices for CRM utilization across the team.
  • Implement sales automation tools and strategies to increase sales team efficiency, from lead generation to closing.
  • Use data and analytics to drive decision-making, improve outreach, and optimize sales cycles.
  • Use advanced sales analytics to manage the sales pipeline effectively.
  • Monitor and analyze sales performance metrics, providing actionable insights and recommendations to optimize sales strategies and team effectiveness.
  • Align with Marketing on pipeline SLAs, lead quality standards, and campaign targeting.
  • Partner with Product to translate sales feedback into roadmap inputs — in this market, the roadmap is a sales tool.
  • Collaborate with Account Management for onboarding handoffs and renewal risk identification.

Benefits

  • Flexible work environment: Remote from your home office, an office in Franklin, TN, if you prefer, or a mix of both.
  • Unlimited vacation time
  • Medical, Dental, and Vision insurance
  • HSA and FSA plans
  • Short-term and Long-term disability
  • Company paid life insurance
  • 401k/Retirement vesting+matching on day 1
  • Performance-based bonuses
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