The Position

We’re looking for a high-energy Upsells & Expansions Account Executive (AE) to drive revenue growth from our existing customer base. In this role, you will proactively identify expansion opportunities, increase product adoption, and work closely with Customer Success to maximize customer value. You’ll be responsible for growing accounts by positioning additional products, increasing contract sizes, and ensuring long-term customer retention.

You will answer directly to the VP of Sales and Success.

What You’ll Do

• Own and execute the upsell and expansion motion for existing accounts, ensuring revenue growth within our customer base.

• Identify and qualify expansion opportunities by analyzing customer usage data, feedback, and business needs.

• Develop and maintain strong relationships with key stakeholders to drive additional product adoption and account growth.

• Partner closely with Customer Success, Product, and Marketing teams to align on strategies for increasing customer lifetime value.

• Lead customer conversations on renewal terms, upsells, and expansion opportunities, ensuring customers understand the value of additional investments.

• Create and deliver compelling sales presentations, business cases, and pricing discussions for upsell and expansion initiatives.

• Maintain accurate records of opportunities, pipeline, and forecast in CRM (e.g. HubSpot).

• Meet or exceed expansion quota and revenue targets.

Requirements

• You embody our eight core values.

• You have 3+ years of experience in Account Management, Expansion Sales, Customer Success, or a similar role in a SaaS environment.

• Comfortable oscillating between strategy and execution with a willingness to get your hands dirty. #own-it

• Experience operating in a high-velocity, non-enterprise, earlier stage business.

• Have a humble, team-oriented approach that gives you the ability to drive growth and results while working closely and collaboratively with all stakeholders.

• Energized by tackling big problems and get excited about opportunities to drive explosive growth and innovation. #solve-it

• Strong ability to uncover customer pain points and align solutions to their business objectives.

• Proven track record of driving upsell and expansion revenue within an existing customer base.

• Data-driven mindset with an understanding of key customer retention and expansion metrics.

• You regularly suggest new ideas, but you also have the ability to prioritize those ideas and execute on them. You can turn plans into execution. You are intrinsically motivated by seeing things become reality. #ship-it

• You are motivated by playing in a competitive market where your skills will be tested.

• You work efficiently and recognize when time is being wasted. #trim-it

• Comfortable working in a remote environment while also driving a collaborative working style. #team-it

• Most of all you act with urgency and choose simple over complex. #ship-it

Bonus Points If You Have

• Have worked at a software company and are comfortable being a part of technical conversations and conveying technical requirements to internal teams.

• Worked with HubSpot

• Background in consultative or value-based selling.

Why You Should Apply:

Competitive Compensation

• Please review our compensation tiers based on your location.

• This role is open to employees only (not contractors).

• We are only able to hire in the following countries: the United States, Canada, and the United Kingdom.

Benefits & Perks

We offer a thoughtfully designed benefits package that balances local standards with Hubstaff’s commitment to flexibility, well-being, and growth. While the exact offerings vary by country, all full-time employees can expect:

• Competitive health and retirement benefits, aligned with local practices (e.g. 401k in the US).

• Paid time off that respects local laws and provides space to recharge.

• Annual stipends to support your home office, professional development, or overall well-being.

• Regular salary reviews tied to performance and growth.

• Ongoing opportunities to grow your career and contribute meaningfully to a remote-first team.

Freedom & Flexibility

• Fully Remote Position: Work from anywhere in the US, UK, or Canada. We are a remote-first, global team that values outcomes over hours.

Unforgettable Retreats

• Celebrate Success Together: Join us for unforgettable annual retreats in stunning locations — past events included the Dominican Republic, Mexico, and Ibiza, Spain. Where will we go next?

Be Part of Our Mission

• Empower the Future of Work: Hubstaff has been remote-first for over 13 years, helping shape the future of work.

• Proven Track Record: We've experienced strong, organic growth and secured our first external investment in 2023 to scale even faster.

• The Best is Yet to Come: Help build what’s next. Your impact here matters — for our product, our customers, and the global workforce.

Company Overview

Our mission is to empower people to have their most productive workday. To do this we have built the industry-leading workforce analytics platform for remote and distributed teams. We were an early believer in the remote work trend and have been one hundred percent remote from day one, which was over a decade ago. With a focus on transparency and accountability, our software provides valuable insights about work habits. Our platform powers time and activity tracking, shift/schedule management, as well as invoicing, and payments for over 95,000 businesses. But we are just getting started. We believe that the remote work trend represents the biggest tectonic shift in the business world since the advent of the PC and that the majority of companies will have a tool like Hubstaff in their tech stack within the next decade. We have a winning culture and want to talk to you about how to help us continue our incredible momentum.