Account Executive (Multi-Product)

The Role

You will be joining our Expansion Sales team, who sells our payments products and all new products through Skimmer such as our new AI phone assistant, bookkeeping, and more. All team members are remote (although Austin-based folks try to come into the office at least once a week) and you will be joining a company with a collaborative culture, focus on customers, and emphasis on having a good time together!

As one of the first Account Executives selling Skimmer's new multi-product solutions, you'll own the full sales cycle across a rapidly expanding product suite (currently, AIPhone, Account/Bookkeeping software, Marketing Suite and Payroll software) . This is a role where Account Executive meets Account Manager: you'll partner to win net-new customers, expand within our existing base, and run upsell and cross-sell motions across both.

You're getting in early, which means you'll help define how we continue to sell these products and you'll grow as our lineup does, because we'll be launching new solutions quickly.

Key Responsibilities

• Customer Outreach & Discovery

  • Engage and qualify both prospective customers and existing Skimmer Pros, tailoring your approach to where each one sits in their relationship with us.

  • Drive high-impact discovery conversations that dig beneath the surface to uncover core pain points, goals, and opportunities, recognizing that discovery is the most critical stage of the buying process.

  • Stay close to a fast-moving product roadmap so you can speak credibly to what's available today and what's coming next.

• Sales Execution

  • Deliver powerful, tailored demonstrations of our multi-product solutions with the explicit goal of attaching payments to every customer account.

  • Act as a business consultant—analytically connecting customer pain points to our solutions, aligning stakeholders, and uncovering needs customers may not even realize they have.

  • Own the sale from start to finish: handle objections with creativity and confidence, involve the right decision-makers, and relentlessly drive toward closing deals, with average deal sizes ranging from $$$ to $$$ annually

• Pipeline Growth & Management

  • Proactively build and manage a disciplined pipeline of opportunities.

  • Collaborate closely with sales, customer success, and marketing teams to strategically drive pipeline growth, improve execution, and share insights that fuel team success.

  • Move deals forward with precision and urgency, ensuring every stage of the pipeline contributes to the ultimate goal of attaching payments and financial products to customer accounts.