We are on the hunt for an accomplished and results-driven Sales Leader to define and lead the sales strategy here at Rustici Software. We are expanding our go to market strategy as part of a strategic growth initiative for the business. You'll work directly with our CEO and the executive leadership team to turn these possibilities into major wins.

This role is a great opportunity for someone to make their mark by helping us establish a new sales channel (outbound) to bring the value of our products to Enterprise and Midmarket customers. While these markets are the priority, additional opportunities to proactively target Content Publishers and Associations are also in play. We have a foundation to build on with highly tenured inbound sales and account management teams, along with a marketing team to provide support. You won't just be managing a team—you'll be the architect, building out the engine that fuels our next chapter.

What you would be selling: Rustici’s software products are designed to solve the technical challenges of content and platform interoperability. We specialize in standards like SCORM and xAPI, and help our customers leverage these standards to improve their commercial products and within larger enterprise learning ecosystems. Our product offerings range from highly complex integrated software to more accessible off-the-shelf products that solve the pain that comes with managing learning and training content at scale across a variety of systems.

The ideal candidate combines deep business development and sales expertise with strong knowledge of sales technology tools and strategies to build and lead a high-performing sales team and develop lasting relationships with C-level executives, HR leaders, and IT decision-makers. Experience in the learning technology space and experience selling early-stage/growth-stage products are also ideal.

Key Responsibilities:

GTM Strategy & Architecture

• 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

Team Building & Leadership

• 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.

Sales Execution & Reporting

• 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
• Sales Insights: 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.

Sales Process & Technology Integration

• 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.

Cross-Functional Collaboration

• 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

Qualifications

• 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

Skills & Capabilities

• 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

We are a remote/in-office hybrid company located in Franklin, TN. While we give preference to local candidates, we are open to qualified remote candidates residing in the United States.

How we’re different

Rustici Software isn’t your average workplace. There’s a reason why we have been named Best Place to Work by Nashville Business Journal for 17 years.

Over the last 20 years, we’ve created a unique environment where people want to work and look forward to Monday. We strive not to be static. Check out “An Open Letter” from our CEO, Tammy Rutherford, to get a better idea of how we work.

Rustici Benefits

We also take great care of the people that work here, and our benefits are unrivaled.

• Flexible work environment: Rustici Software offers the best of all worlds when it comes to where you work. Remote from your home office, an office in Franklin, TN, if you prefer, or a mix of both. We care more about the work that you do than where you do that work.
• 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

How to Apply

• Tell us why you want to work with us.
• Explain what you can bring to our team.
• Include your resume, portfolio, or whatever best represents your experience.

Each time we hire, we wait until we find exactly the right person. If that’s you, we really hope you’ll apply. Make sure that what we get from you makes it apparent that you are the right person for the job, and that you want to work here, not just somewhere.