Director, Inside Sales

Tekion

3d • $93,000 - $155,000 • Remote

About The Position

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 be responsible for driving ARR growth through upsell and cross-sell motions, increasing SKU penetration, and building a scalable inside sales engine focused on maximizing customer value and product adoption.

This role requires a strong commercial leader who can combine growth strategy, sales process discipline, operational rigor, and team leadership to deliver measurable results. The ideal candidate brings deep experience leading inside sales or account growth teams, managing performance through detailed KPI reporting, and building repeatable motions that accelerate expansion revenue across an installed base.

Requirements

• 8+ years of experience in inside sales, account growth, renewals, business development, sales leadership, with 5+ years leading managers and high-performing sales teams
• Proven track record of owning and delivering expansion revenue growth within an existing customer base
• Demonstrated success driving growth, upsell performance, cross-sell execution, and SKU penetration across current accounts
• Strong expertise inside sales process design, pipeline management, forecasting, KPI reporting, and performance optimization
• Experience managing performance at multiple levels, including department, product/SKU, team, and individual associate metrics
• Highly analytical with the ability to translate performance data into actionable growth strategies and operational improvements
• Strong cross-functional leadership skills with experience partnering across 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

Nice To Haves

• Experience leading sales teams focused on installed base growth, recurring revenue expansion, or multi-product account penetration
• Background in SaaS, automotive technology, retail technology, or other complex B2B subscription environments
• Experience managing large books of business with accountability for ARR growth and product adoption across a diverse customer base
• Strong executive communication skills with experience presenting business performance, forecasts, and growth strategies to senior leadership

Responsibilities

• Lead the strategy and execution for inside sales growth across Tekion’s existing dealer customer base, with primary responsibility for 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 focused on growing revenue within current accounts 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 department-level, SKU-level, and associate-level KPI management to drive accountability, visibility, and consistent execution
• Monitor and analyze key 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 closely with Customer Success, Account Management, Product, Marketing, and Revenue Operations to identify growth opportunities, align account strategies, and improve expansion outcomes
• Design and implement targeted growth plays by product, SKU, customer segment, and business opportunity to increase adoption within the installed base
• Provide executive-level reporting and business insights on performance, trends, risks, and opportunities across the inside sales growth function
• Drive process standardization, CRM discipline, pipeline hygiene, and reporting accuracy to improve sales efficiency and decision-making
• Lead organizational planning including hiring, onboarding, coaching, talent development, capacity planning, and succession planning to support long-term growth
• Serve as a key leader within the broader go-to-market organization, influencing strategy, tooling, and cross-functional initiatives that support customer revenue expansion

Benefits

• Competitive compensation and generous stock options
• 100% employer-paid top-of-the-line medical, dental and vision coverage
• Great benefits including unlimited PTO, parental leave and free snacks and beverages
• The opportunity to work with some of the brightest minds from Silicon Valley’s most dominant and successful companies
• Be part of an early stage, hyper-growth start-up with the opportunity to grow and prosper
• Work on the latest and coolest technologies – everything is home-grown and built ground-up
• A dynamic work environment with a strong sense of community and collaboration
• The open and transparent culture that encourages innovation, rewards performance and discourages hierarchy
• Exciting opportunities for career growth and development

What This Job Offers

• Job Type: Full-time
• Career Level: Director