Director, Inside Sales

About the Role

The Director, Inside Sales – Growth & Upsell will lead Tekion’s strategy and execution for expanding revenue within the existing dealer customer base across the U.S. and Canada. This leader will drive ARR growth through upsell and cross-sell motions, increase SKU penetration, and build a scalable inside sales engine focused on maximizing customer value and product adoption.

Responsibilities

• Lead the strategy and execution for inside sales growth across Tekion’s existing dealer customer base, focusing on upsell, cross-sell, ARR expansion, and SKU penetration.
• Own performance against expansion revenue targets, including growth by dealer, SKU, region, team, and individual associate.
• Build and scale a high-performing inside sales organization through proactive outreach, value-based selling, and disciplined opportunity management.
• Develop and optimize the end-to-end sales process for customer expansion, including account prioritization, opportunity identification, outreach strategy, pipeline progression, proposal management, and close.
• Establish a rigorous operating cadence with clear KPI management at department, SKU, and associate levels.
• Monitor and analyze metrics such as ARR growth, SKU attach rates, product penetration, pipeline creation, conversion rates, average deal size, activity productivity, forecast accuracy, and rep attainment.
• Partner with Customer Success, Account Management, Product, Marketing, and Revenue Operations to identify growth opportunities and align strategies.
• Design and implement targeted growth plays by product, SKU, customer segment, and business opportunity.
• Provide executive-level reporting and insights on performance, trends, risks, and opportunities.
• Drive process standardization, CRM discipline, pipeline hygiene, and reporting accuracy.
• Lead organizational planning, including hiring, onboarding, coaching, talent development, capacity planning, and succession planning.
• Serve as a key leader within the go-to-market organization, influencing strategy and cross-functional initiatives.

Qualifications

• 8+ years of experience in inside sales, account growth, renewals, business development, or sales leadership, with 5+ years leading managers and high-performing teams.
• Proven track record of delivering expansion revenue growth within an existing customer base.
• Demonstrated success in driving growth, upsell, cross-sell, and SKU penetration.
• Strong expertise in sales process design, pipeline management, forecasting, KPI reporting, and performance optimization.
• Highly analytical with the ability to translate data into actionable strategies.
• Strong cross-functional leadership skills and experience partnering with Customer Success, Account Management, Product, Marketing, and Revenue Operations.
• Deep experience with CRM systems, dashboards, and reporting tools; Salesforce expertise required.
• Bachelor’s degree in Business, Sales, Marketing, or related field preferred.
• Central or East Coast time zone preferred.

Preferred Qualifications

• Experience leading sales teams focused on installed base growth or recurring revenue expansion.
• Background in SaaS, automotive technology, retail technology, or complex B2B subscription environments.
• Experience managing large books of business with accountability for ARR growth and product adoption.
• Strong executive communication skills with experience presenting to senior leadership.

Benefits

• Competitive compensation and generous stock options.
• 100% employer-paid medical, dental, and vision coverage.
• Great benefits including unlimited PTO, parental leave, and free snacks and beverages.
• Opportunity to work with top talent from leading Silicon Valley companies.
• Be part of an early-stage, hyper-growth startup with career growth opportunities.
• Work on cutting-edge, homegrown technologies.
• Dynamic, collaborative work environment with a strong sense of community.
• Open, transparent culture that encourages innovation and rewards performance.

Compensation Range: $93K - $155K