Payroll Inside Sales – Outbound

Summary 

We are seeking a driven and results‑oriented Payroll Inside Sales Representative to join our Outbound Sales team. In this role, you will proactively engage prospects through outbound calling, targeted outreach, and strategic follow‑up to generate new business opportunities. In addition, you will also be responsible for identifying upsell, cross‑sell, and expansion opportunities within our existing client base. You’ll uncover business needs, showcase additional value, and guide both prospects and customers through the sales cycle with professionalism and persistence. 

Key Responsibilities 

• Conduct high‑volume outbound calls, sequences, and targeted outreach to generate qualified opportunities. 

• Identify and engage decision‑makers, uncover business challenges, and assess fit for payroll solutions. 

• Execute outbound prospecting strategies while also upselling and expanding relationships with existing clients. 

• Proactively reach out to current customers to introduce additional payroll services, new product features, and value‑add solutions. 

• Deliver consultative product overviews and demonstrations (phone, web, or video) to advance both new and existing‑client opportunities. 

• Build and manage a robust pipeline—including outbound prospects and upsell accounts—with consistent follow‑up and accurate customer relationship management documentation. 

• Collaborate with Sales Leadership, Marketing, and Client Success on account expansion strategies and outbound initiatives. 

• Partner with Implementation and Client Success teams to ensure seamless transitions for new and expanded clients. 

• Meet and exceed KPIs for outbound activity, pipeline creation, upsell revenue, and closed deals. 

• Stay informed on payroll compliance, tax requirements, HR technology, and industry trends to support deeper conversations with both prospects and existing clients. 

• Represent the company with confidence, professionalism, and a high‑effort mindset. 

Qualifications 

• 1–3 years of Outbound Sales, SDR/BDR, Inside Sales, Account Management, or Business Development experience (ideally in Payroll, HR, SaaS, or Financial Services). 

• Demonstrated success generating pipeline and exceeding outbound or upsell targets in a consultative sales environment. 

• Strong communication, persuasion, and objection‑handling skills. 

• Ability to manage a high‑volume day while staying organized across outbound prospects and existing client conversations. 

• Proficiency with CRM tools (e.g., Salesforce, Gong) and outbound engagement platforms. 

• Knowledge of payroll processes, HR systems, or related solutions is highly preferred. 

What We Offer 

• Competitive base salary plus unlimited earning potential (new business + upsell). 

• Comprehensive benefits package (health, dental, vision, retirement). 

• Ongoing training, development, and career progression. 

• A collaborative, supportive team focused on growth and performance. 

Candidates should be comfortable with an on-site presence to support collaboration, team leadership, and cross-functional partnership.

Why Join Us:

At Acrisure, we’re building more than a business, we’re building a community where people can grow, thrive, and make an impact. Our benefits are designed to support every dimension of your life, from your health and finances to your family and future.

Making a lasting impact on the communities it serves, Acrisure has pledged more than $22 million through its partnerships with Corewell Health Helen DeVos Children's Hospital in Grand Rapids, Michigan, UPMC Children's Hospital in Pittsburgh, Pennsylvania and Blythedale Children's Hospital in Valhalla, New York.

Employee Benefits

We also offer our employees a comprehensive suite of benefits and perks, including:

• Physical Wellness: Comprehensive medical insurance, dental insurance, and vision insurance; life and disability insurance; fertility benefits; wellness resources; and paid sick time.

• Mental Wellness: Generous paid time off and holidays; Employee Assistance Program (EAP); and a complimentary Calm app subscription.

• Financial Wellness: Immediate vesting in a 401(k) plan; Health Savings Account (HSA) and Flexible Spending Account (FSA) options; commuter benefits; and employee discount programs.

• Family Care: Paid maternity leave and paid paternity leave (including for adoptive parents); legal plan options; and pet insurance coverage.

• … and so much more!

This list is not exhaustive of all available benefits. Eligibility and waiting periods may apply to certain offerings. Benefits may vary based on subsidiary entity and geographic location.

Acrisure is an Equal Opportunity Employer. We consider qualified applicants without regard to race, color, religion, sex, national origin, disability, or protected veteran status. Applicants may request reasonable accommodation by contacting [email protected].

Final candidates will be required to complete post-offer verification processes related to the role and in accordance with applicable laws.

California Residents: Learn more about our privacy practices for applicants by visiting the Acrisure California Applicant Privacy Policy.

Recruitment Fraud: Please visit here to learn more about our Recruitment Fraud Notice.

Welcome, your new opportunity awaits you.