Sales Lead at Expensify

Your Mission, Should You Choose To Accept It

Join our passionate sales team solving real-world problems and helping people spend less time on expenses, more time on what matters. We're building the easiest, fastest platform to automate everything expense-related.

This is a unique leadership opportunity: You'll step into a high-impact role and establish yourself as a key leader in a flat organization with significant growth ahead.

About You 

We're looking for an experienced SaaS sales leader who can do it all. You'll manage a team of account executives and onboarding specialists, control conversion metrics for your pod, nurture our established partner channels for lead generation, and weigh in on roadmap decisions based on what you learn from customers on the front lines. The Expensify Sales team delivers an exceptional full-cycle experience—from lead generation and account management to addressing client concerns and driving long-term success.

Experience & Background:

• 5+ years of SaaS B2B sales with proven team management success and results

• Strong CRM skills (HubSpot ideal, other platforms work too)

• Exposure to strategic channels or partner management for lead generation (or willingness to learn, we can teach the specifics!)

• Ready to step into a VP-level leadership role from day one

What Makes You Successful in This Role:

• You have a track record of coaching and developing sales talent, with the ability to motivate others to exceed their goals

• You have relationships with accounting firms or similar partnerships, or demonstrated success building these from scratch

• You are able to discover and teach yourself the nuanced details of a complex, continuously changing product serving a sophisticated, international accounting audience

• You have strong attention to detail and an understanding of how small mistakes can have a large impact. You use this skill to improve processes making them more efficient and scalable

• You are a skilled communicator in both written and verbal format with the ability to simplify complex sales or product details for customers and teammates

• You thrive in an environment with minimal supervision and can stay on task and find ways to fill your extra time constructively without a direct manager

• You embrace change when the company changes and grow to ensure you get better year after year

• You collaborate with enthusiasm and humility, without regard for whose idea is best, and celebrate being wrong as an opportunity for self-improvement

• You’re excited by our culture of Live Rich, Have Fun, and Save the World, and have an ambition you’re incredibly passionate about that Expensify can help you achieve
  

Daily Focus & Responsibilities

Lead & Sell:

• Coach and mentor Guides to become top performers. Create programs to support their growth and success

• Build and strengthen relationships with accounting firm partners

• Own conversion metrics for your pod, driving team performance and individual success

• Convert new leads into paying customers by engaging meaningfully with prospects and showcasing our product’s best-in-class features

• Provide tailored support and solutions to address specific pain points for prospective customers

• Help set the standard for best practices by selling new products and features successfully, providing the foundation for team-wide scaling

• Scale positive experiences across partner accounting firms and their clients through seamless communication and feature integration

• Nurture strategic channels for lead generation

Collaborate on Product Initiatives:

• Articulate and document product feedback from customers and leads, clearly identifying areas for improvement

• Partner with our Product team to find and create solutions to challenges raised by customers or your fellow teammates, contributing valuable insights from a sales perspective

• Participate actively in product discussions, ensuring customer needs are represented

Leadership:

• Set the bar for excellence, sharing your sales strategies and encouraging others to adopt best practices

• Assist in managing team responsibilities, ensuring seamless collaboration across the team

Level Up the Team:

• Identify areas where our sales processes can be improved—whether they’re outdated, over-complicated, or just not cutting it

• Champion the effective use of sales tools like HubSpot and Gong, especially as we integrate new ones

• Bring a creative mindset to your team, encouraging experimentation with new sales strategies and techniques to stay ahead of the curve

What Makes This Opportunity Special

This is more than just a sales leadership role—it's a chance to establish yourself as a key leader in a high-growth environment:

• Flat Organization: Direct impact and visibility across the company

• Fully Remote: Work from anywhere in the US with hyper-flexible work arrangements

• Grow Your Impact: Build and define this leadership role in a flat organization where ownership, scope, and compensation grow with your contributions, not just titles

• Own Your Success: Control conversion metrics for your pod and directly influence outcomes

Compensation & Benefits

• Full-time salaried position with total compensation of $135,000 - $225,000 (salary + equity), with additional commission opportunity based on performance

• 401k with employer match

• 100% medical, dental, vision, and mental health coverage

• $20k annual family planning benefit through Carrot

• Up to three months of fully paid parental leave, with up to six months for birthing parents

• Commuter benefits

• Flexible vacation policy

Next Steps

Like what you see? Applying is easy, but it takes time. See, while we know you're awesome, it's actually really hard and time-consuming to find you in the midst of literally hundreds of other applications we get from everyone else. So this is where we're going to ask our first favor: can you make it really easy and obvious how great you are, so we don't accidentally overlook you? There are many ways to do that, but the easiest way to help us out is by answering the following questions:

1. Share your LinkedIn profile and tell us—what got you into sales in the first place? What have you been doing since then?

2. What is your proudest success story from managing or coaching a sales team? What did you do, and what difference did it make?

3. Which CRM platforms have you used, and how comfortable are you with HubSpot specifically? Can you share an example of how you’ve used CRM tools to improve your team’s performance or sales process?

4. What do you want to do with the rest of your life, and how is Expensify a step toward your long-term goals? (We’re serious, we want to know! Share what you’re comfortable sharing, but we are a group of ambitious individuals building a community of people who want to achieve success in every aspect of our lives, and we encourage employees to figure out how they can use Expensify to realize their personal goals with the support of the company around them.)

5. How did you hear about us? A job posting? Chalk on a sidewalk? From a friend? Let us know where you saw this opening.

We’re committed to providing a fair and inclusive hiring experience. If you need a reasonable accommodation at any stage of the process, just let us know—we’re happy to help