Account Executive (Multi-Product)

We’re looking for an Account Executive (Multi-Product) who is a proven salesperson, ideally in SaaS, who thrives in full-cycle selling—sourcing, qualifying, and closing deals end-to-end. You’re naturally curious with strong discovery and analytical skills, and you know how to translate customer needs into clear solutions. Strong organizational skills and pipeline discipline are a must, and experience with HubSpot or another CRM will help you hit the ground running. You’re not afraid to pick up the phone and you believe that making an extra 10 calls is the difference between hitting and missing quota. Above all, you’re a kind human who easily adapts to change and embraces the opportunity to help shape how we sell and scale new financial products.

The Team: 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!

What you'll do:

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.

1. 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.

2. 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.

3. 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.

What you bring:

• Full-cycle B2B SaaS sales experience with consistent quota attainment or overachievement
• Proven ability to prospect, qualify, and close deals end-to-end
• Comfort building without a playbook: you can sell a product that doesn't yet have proven pitches, case studies, or a polished objection-handling library, and that challenge energizes you rather than rattles you.
• Proficiency with CRM systems (HubSpot preferred) and sales tools
• Exceptional written and verbal communication skills; able to build rapport across all levels of an organization
• A strong feedback loop instinct: you synthesize what you hear in the field and bring it back to product, marketing, and leadership in a structured way that shapes positioning, pricing, and roadmap.
• Strong organizational skills with the ability to manage time, pipeline, and priorities in a fast-paced environment
• Analytical, resourceful, and creative in solving problems and overcoming objections
• Learning agility: you ramp fast on new products and can get credible on something you've never sold before, quarter after quarter, as our product suite evolves.
• Tenacious, curious, and highly adaptable, with the drive to thrive as a founding seller in a brand-new motion.

Bonus Points:

• Previous experience selling vertical SaaS products to service-based businesses or field service management software
• Knowledge of the pool service industry or related home service businesses

Benefits

• Competitive base pay + bonus potential
• Generous medical, dental, and vision plans (we pay 100% of your premium and 50% of your dependents’)
• Fantastic culture with a very strong eNPS—we work hard, celebrate wins, and learn as we go to always be improving to benefit our customers.
• Immediate access to 401(k) with company match
• Flexible PTO (MINIMUM of 10 days required every year)
• 12 weeks paid parental leave for birthing parent, 6 weeks paid leave for supporting partner
• Remote work friendly
• Comprehensive learning and development budget
• A manager dedicated to your development