Account Executive, Upsell

About the Role

We’re looking for an Account Executive to help expand and scale our revenue within our existing customer base at Steer. In this full-cycle role, you will focus on identifying new opportunities in your book of accounts, conducting outbound calls, demonstrating software solutions, and closing upgrades for Steer CRM and our phones product.

This is an active, driver-seat sales role. You will be expected to learn how each shop operates, build trust with small business owners, and make a compelling case for additional platform features. We are looking for someone who takes full ownership of their pipeline, thrives in a high-volume outbound motion, and loves growing revenue within an established customer base.

 

This is a remote role.

Compensation: $120,000 OTE ($60,000 base salary + commission)

 

You Are

• A Self-Starter: You enjoy prospecting, take end-to-end ownership of your pipeline, and comfortably drive sales opportunities forward.
• Empathetic & Professional: You understand the reality of busy small business owners and can explain software benefits in clear, practical terms.
• Resilient & Persistent: You excel at handling objections, making outbound calls, and building momentum through consistent follow-through.
• A Strong Communicator: You excel at discovery, lead engaging product demonstrations, and confidently communicate value across all stages of a deal.
• Organized & Disciplined: You maintain meticulous pipeline records, manage customer conversations effectively, and follow up thoroughly.
• Coachable: You are self-directed, open to feedback, and driven to achieve and exceed your revenue quota.

 

You Will

• Drive Account Expansion: Proactively call and engage existing Steer customers to uncover and close CRM and phones product upgrades.
• Manage Full Sales Cycle: Own the entire journey from initial outreach and discovery through product demos, proposals, negotiations, and closing.
• Consultative Selling: Learn each shop’s goals and workflows to demonstrate how Steer’s platform directly solves their operational pain points.
• Pipeline Management: Maintain an active, healthy pipeline with accurate forecasting and up-to-date opportunity records in the CRM.
• Partner for Success: Collaborate with customer-facing teams to review account history and ensure a smooth customer experience post-sale.

 

You Have

Must Have:

• Sales Ownership: Proven experience owning and closing full-cycle sales opportunities, ideally in an expansion or account growth role.
• Outbound Confidence: Comfortable making proactive calls to generate revenue opportunities rather than relying on inbound leads.
• Core Sales Skills: Strong discovery, presentation, objection-handling, negotiation, and closing capabilities.
• Quota Track Record: Self-directed mindset with a history of meeting or exceeding activity and revenue goals.

 

Nice to Have:

• SaaS & Product Background: Experience selling SaaS, CRM, communications, or phone solutions.
• Account Expansion: Prior success growing revenue and expanding platform usage within an existing customer base.
• Industry Experience: Familiarity with automotive repair shops, home services, or other service-oriented businesses.

 

Interview Process

• Initial Screen (Lead Recruiter) — 30 min
• Executive Interview (Head of Sales) — 30 min
• Hiring Manager Interview (Sr. Sales Manager) — 30 min
• Problem Solving Interview (Director of People) — 60 min
• Reference Checks

 

We Offer

• 100% remote work
• 100% employer-paid medical insurance
• Flexible PTO with a 15-day minimum
• Generous parental leave
• FSA and HSA plans
• Equity options
• 401(k)
• Learning stipend
• Work-from-home equipment setup
• High-ownership culture with clear opportunities for career growth