Sales - Account Executive

Sales - Account Executive

We’re seeking a driven and entrepreneurial Account Executive to help lead the charge in growing our payroll revenue. In this role, you will drive payroll upsell opportunities within a portfolio of existing customers and support them through implementation and their first payroll run. You’ll play a vital part during our high-impact year-end selling season and have the opportunity to grow into a sales leadership role in 2026.

This role is intentionally designed to anticipate transitioning into a Sales Leadership role within six to nine months. Our ideal candidate will be able to initially demonstrate strong boots-on-the-ground sales efforts before transitioning to a leadership/management position and building out our payroll sales department from the ground up.

This base plus commission role is ideal for a hands-on seller with leadership ambition who thrives in a fast-paced, collaborative environment.

Responsibilities

• Upsell Execution: Drive expansion within the assigned book of business by promoting our payroll solution to existing customers by conducting discovery calls and product demonstrations.


• Account Growth Strategy: Develop strategic account plans to identify growth opportunities, align with customer goals, and achieve revenue targets.


• Quota Achievement: Meet or exceed upsell targets, contributing directly to the company’s revenue goals.


• Lead Generation & Pipeline Development: Source and qualify new leads to build a strong pipeline; pursue outbound opportunities where appropriate.


• CRM Management: Maintain accurate and up-to-date records of customer interactions, opportunities, and pipeline activity in the CRM (e.g., Salesforce, HubSpot).


• Cross-functional collaboration: Partner with Customer Success, Product, and Support teams to resolve issues, deliver value, and support customer initiatives. Work internally to improve customer experience and product/industry knowledge


• Product Expertise: Develop a deep understanding of our time tracking and payroll solutions to effectively demonstrate value and answer customer questions.

Required Qualifications

• Payroll Sales Experience: 18 months+ experience successfully selling payroll, at a known payroll provider/solution, ideally in a SaaS or technology environment.


• Consultative Sales Skills: Proven ability to drive upsell opportunities by uncovering customer needs and aligning solutions.


• Communication: Excellent interpersonal, verbal, and written communication skills.


• Results-Oriented: A track record of meeting or exceeding revenue targets in a commission-based role.


• AI Fluency: Proven ability to leverage AI tools (e.g., ChatGPT, Apollo AI, Lavender, Clay, etc.) to enhance outbound efforts, personalize pitches, optimize workflows, and accelerate pipeline velocity. 


• Analytical Skills: Ability to analyze customer data and usage trends to inform account strategies.


• Sales Process: Experience managing sales processes and tools to support a growing sales team. Track record of accurate and timely adherence to deal tracking within CRM systems (e.g., Salesforce, HubSpot).


• Self-Starter: Ability to independently and aggressively source and develop new leads.


• Leadership Track Commitment: Clear ambition and readiness to transition into a leadership role; prior experience developing or scaling a sales team is a strong plus.


• Leadership Experience: Prior experience managing or mentoring a high-performing sales team (e.g., SDRs and SMB/Mid-Market reps) is a strong plus.


• Industry Knowledge: Familiarity with time tracking and workforce management platforms.


• Department Building: Experience building a sales department from the ground up. You must be the expert in the room on building the department, strategy, goal setting, building a team, and anything else needed to build out a new sales department.

You're wondering, what is OnTheClock?

OnTheClock, founded in 2004, is a Michigan-based SaaS company that provides businesses with workforce management tools, such as time tracking, scheduling, and payroll. Our platform provides employers with a simple way to track employee hours, establish work schedules, and pay employees in one system. OnTheClock has a great culture, and we are looking for like-minded people to offer the best service possible for our customers.

What we look for in you

• Positive - whatever it takes attitude


• Analytical - drills down into data and loves technology, data, and spreadsheets


• Growth Mindset - curious and always learning


• Deep Expertise – You bring a level of skill and insight that elevates our team.


• Build Up Others - teach others as you work


• Results Focused - ability to achieve and prove results


• Culture Fit - Must fit in here at OTC, in line with our values - https://www.ontheclock.com/meetUs.aspx#our-values


• Be A Doer - always looking for new ways to look at data and make recommendations


• Find us on LinkedIn to understand more about who we are

Why Should You Work Here With Us

• Award-Winning Culture - Recognized as a Crain’s Best Place to Work in 2023 & 2024

• Competitive pay plus 401k that includes employer contributions on day 1


• Comprehensive Benefits – 100% paid health insurance, dental & vision (Blue Cross), $100K life insurance, short & long-term disability 


• Work-Life Balance – Paid time off + 9 paid holidays


• Perks & Growth – Free company lunch (Thursdays), stocked kitchen, $1,000 annual education support


• Strong Reputation – 4.9-star Glassdoor rating & 4.8-star product review

The fine print

• An I-9 form will be required to be completed at hire to confirm work authorization.


• If you require reasonable accommodation to complete this application, contact [email protected].