Director of Field Sales
Serving over 5,000 small businesses today, we aspire to be the most relied-upon partner a business owner never has to think about. From Hourly Time Tracking and Time Clock software to Scheduling and automated Payroll and HR, we've built an easy-to-use platform with features that save our customers time and money.
Role Overview:
We’re looking for a high-impact, high-energy Director of Field Sales to lead our outbound-driven sales organization focused on helping small and mid-sized businesses transform the way they manage payroll, HR, and people operations.
This is a hands-on leadership role for a sales builder - someone who loves developing teams, driving activity, and creating a winning outbound culture. You’ll be responsible for building and leading regional field teams, building new business pipelines, and equipping your sellers to win in a competitive and fast-moving market.
If you’re a strategic sales leader who thrives on prospecting, coaching, and creating new opportunities, not waiting for inbound leads, we want you on our team.
Whether remote or working from our Brooklyn or Chicago-based offices, you'll find a team-oriented environment where our Core Beliefs matter:
Reliable
Optimistic
Compassionate
Knowledgeable
[A good sense of humor helps, too!]
This role reports to the Chief Revenue Officer.
What You’ll Do
Lead & Inspire
Lead, develop, and motivate regional and field sales managers to consistently exceed new business targets.
Build a performance-driven culture centered around proactive prospecting, outbound activity, and pipeline creation.
Drive accountability across teams through clear goals, metrics, and consistent coaching.
Foster collaboration with marketing, sales enablement, and product teams to amplify market impact.
Drive New Business Growth
Own the outbound sales strategy, from territory planning to prospecting execution.
Ensure every field team is effectively generating pipeline through cold outreach, local networking, and community engagement.
Coach teams to master a consultative, value-based sales approach, positioning our payroll and HR platform as a critical solution for SMB and mid-market clients.
Partner with Marketing to develop regional campaigns and field events that attract and convert new customers.
Operational Excellence & Performance Management
Set ambitious but achievable sales goals and ensure teams are meeting or exceeding activity benchmarks (calls, meetings, demos, etc.).
Track performance through CRM and sales analytics tools, using data to identify trends and opportunities for improvement.
Streamline sales processes to improve efficiency and close rates.
Manage budgets, staffing, and forecasting to ensure scalable, predictable growth.
Market Leadership
Stay ahead of market trends, competitive shifts, and SMB buyer needs within the Payroll & HR tech space.
Represent the company at regional events, conferences, and trade shows to build brand awareness and generate leads.
Build strong relationships with strategic partners, referral networks, and industry associations to drive market penetration.
Key Skills and Qualifications
10+ years of progressive B2B sales experience, including 5+ years leading field or regional sales teams.
Proven success driving outbound, prospecting-led sales in the Payroll, HR, or HCM industry (experience with competitors like ADP, Paylocity, Paycor, Paychex, Gusto, etc. a plus).
Deep understanding of the SMB and Mid-Market sales motion - from cold outreach to executive-level negotiation.
Exceptional leadership and coaching skills; able to inspire performance and hold teams accountable.
Strong data and pipeline management capabilities using CRM systems (e.g., Salesforce). A competitive mindset with a passion for winning new business and developing people.
Willingness to travel up to 40–50% to engage with field teams, prospects, and customers.
Who You Are
A builder: you create structure, process, and results from the ground up.
A hunter: you know the value of daily prospecting and love driving outbound motion.
A coach: you motivate your team to hit goals, overcome objections, and keep the energy high.
A strategic leader: You understand the big picture and know how to execute at scale.
Why You’ll Love It Here
Competitive base salary plus commissions and performance incentives.
Comprehensive benefits package (medical, dental, vision, 401(k), etc.).
Career growth in a high-growth, innovative HR tech company.
A passionate, fast-paced culture that rewards initiative and results.
Company Conformance Statement
In performance of their respective responsibilities, all employees of Fingercheck are expected to:
Complete quality work within deadlines.
Interact professionally with other employees, customers, and suppliers.
Work effectively as a team contributor on all assignments.
Communicate and coordinate work efforts with other employees, customers and suppliers.
Perform other duties as assigned.
Attend work regularly based on the assigned schedule.
About Fingercheck
At Fingercheck, we're about making life easier for small business owners. We know payroll and HR can be a total headache, so we created a platform that simplifies everything. You can say goodbye to the stress and time-consuming tasks of payroll and HR management, including taxes and compliance – we've got you covered!
Our advanced AI and automation technology saves you time and money, so you can put energy into growing your business. And the best part? Our team is dedicated to providing top-notch support. We take the time to understand your needs and offer personalized solutions to make your internal processes quick, easy, and accurate.
For more information, please visit fingercheck.com or follow us on LinkedIn, Facebook, Twitter & Instagram.
Disclaimer
Fingercheck is an equal opportunity employer that values diversity, inclusion, and belonging. We do not discriminate on the basis of race, religion, color, national origin, gender, gender identity or expression, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.