Digital Sales Advisor

At Justworks, we help small businesses confidently navigate the complexities of running a business—from payroll and benefits to HR, compliance, and workforce management.

More small business owners are beginning their Justworks journey digitally. Many can evaluate and purchase Justworks through Self-Service. Others reach a point where having a knowledgeable person available can make the difference between getting stuck and confidently moving forward.

That’s where Digital Sales comes in.

The Role

As a Digital Sales Advisor, you will work with small business owners and administrators who are already engaging with Justworks digitally and where human guidance can help them take the next step.

This is not a traditional lead qualification role, and you won’t spend your day collecting information so someone else can sell to the customer. It also isn’t an order-taking role.

You will quickly understand what the customer is trying to accomplish, determine what is preventing them from moving forward, and take action.

Sometimes that means answering a benefits or payroll question and helping the customer continue through Self-Service. Sometimes it means helping them compare options, configure the right Justworks solution, and owning the sale through close. And sometimes it means recognizing that the customer’s needs require deeper expertise and making a seamless transition to Managed Sales.

Your job is simple: make it easier for small businesses to confidently choose and buy Justworks.

Your Success Profile

What You Will Work On

• Engage with small business owners and administrators who have demonstrated interest or intent through the Justworks digital buying experience.
• Use customer and behavioral signals to prioritize where your time and expertise can have the greatest impact.
• Quickly understand customer readiness, needs, urgency, and complexity.
• Conduct focused discovery that gets to the customer’s real question without unnecessarily extending the sales process.
• Advise customers across common payroll, benefits, HR, compliance, and workforce questions.
• Help customers understand which Justworks products best fit their needs and identify opportunities to sell the broader platform where appropriate.
• Explain pricing and value clearly and confidently.
• Understand the alternatives customers are considering and position Justworks effectively.
• Handle objections and confidently ask for the business when the customer is ready to buy.
• Work alongside customers to complete important steps rather than simply giving them another list of things to do.
• Own appropriate opportunities through conversion and create a smooth transition into onboarding.
• Resolve discrete questions or blockers and help customers continue through Self-Service when that is the best experience.
• Recognize when customer complexity warrants Managed Sales and make a seamless, context-rich transition.
• Recognize when a customer has genuine future potential but isn’t ready to buy today and move them into the appropriate nurture experience.
• Use AI and automation to prepare for conversations, understand customer context, complete follow-up, and minimize administrative work.
• Capture clean customer signals and outcomes so we can continuously improve how customers buy Justworks.
• Share recurring customer questions, objections, and friction with the teams improving our digital and Self-Service experiences.
• Participate in experiments around customer signals, timing, messaging, sales plays, and workflows—and help us understand what actually improves customer and commercial outcomes.

How You Will Do Your Work

Be consultative and commercial. You don’t read a script or run every customer through the same discovery process. You listen, diagnose, advise, and sell.

Create momentum. Every customer interaction should move the buying journey forward with a clear outcome and next step.

Use judgment. You know when to sell, when to solve the immediate problem, when to bring in deeper expertise, and when a customer simply isn’t ready yet.

Do the work with the customer. If helping a customer work through a quote, understand a contribution model, complete an application, or navigate another step gets them unstuck, you lean in and help.

Learn broadly. Small business owners don’t organize their questions around our internal teams. You develop enough knowledge across Justworks’ products to understand the problem, answer common questions, and get customers to the right outcome quickly.

Embrace technology. AI and automation are core to how this team operates. You use them to eliminate administrative work and spend more time helping customers.

Experiment and improve. Digital Sales is a new motion. You will help us test and improve how we engage customers, and some of the work you do today may eventually become automated or built directly into the product. That’s success.

What We’re Looking For

• Experience in a quota-carrying sales or other customer-facing commercial role; experience in high-velocity SMB, inbound, digital, or product-led sales is especially relevant.
• Demonstrated ability to understand customer needs and translate them into a clear recommendation.
• Strong communication skills and comfort advising small business owners and decision-makers.
• Commercial instinct—you recognize buying signals, can handle objections, and are comfortable asking for the business.
• Ability to learn products quickly and explain complex concepts simply.
• Bias toward action and a willingness to work alongside customers to solve problems and keep them moving.
• Strong organization and follow-through in a fast-moving environment.
• Comfortable using CRM systems, customer data, AI, and automation as part of your daily workflow.
• Curious, adaptable, and energized by helping build something new.
• Experience with payroll, benefits, HR, PEO, fintech, SaaS, or SMB customers is helpful but not required.
• Willingness to work from our Phoenix office as part of an in-person team.

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