Digital Sales Advisor

Justworks; Tampa (FL); Remote; USD 60,000 - 90,000; Full time

Benefits offered by this job

Paid volunteer work

Paid parental leave

Work from home

Medical/dental/vision insurance

Wellness stipends

Equity

Learning & development

Apprenticeship program

Job summary

Justworks is seeking a Digital Sales Advisor to work with small business owners who are already engaging with Justworks digitally. You will guide them through questions, compare options, and own the sale through close.

In this role you run discovery, explain pricing, and decide when to escalate to Managed Sales or onboarding, always aiming to move the buyer forward with clarity and confidence. Comfort with CRM, AI-assisted workflows, and a preference for helping small businesses arrive at the

Qualifications

• Experience with payroll, benefits, HR, PEO, fintech, SaaS, or SMB customers is helpful but not required.
• Quota-carrying sales or other customer-facing role
• Strong organization and follow-through in a fast-moving environment

Responsibilities

• Engage with small business owners and admins to understand needs and guide self-service buying.
• Advise on payroll, benefits, HR, and related Justworks products.
• Identify objections, explain pricing, and drive opportunities to close.
• Coordinate with onboarding when customers convert to paid.
• Use AI and automation to prepare for conversations and minimize admin work.
• Move high-potential prospects to Managed Sales when deeper expertise is needed.

Skills

CRM systems

AI & automation

Strong communication

Sales experience

Inbound/digital sales

SMB focus

Tools

CRM software

Salesforce

Analytics tools

Job description

• 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
• 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
• 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

Benefits

• Paid volunteer work
• Paid parental leave
• Work from home opportunities
• Medical, dental, and vision insurance, plus access to One Medical, Kindbody, and Teladoc
• Premium access to Headspace, ClassPass stipends, and webinars to support your overall wellness on topics like nutrition, budgeting, mindfulness, and more
• All Justworks offers include equity, and Justworkers can continue to earn more over time with promotions and tenure
• Extensive learning & development opportunities through workshops, ExecOnline, Udemy, and BetterUp coaching
• Apprenticeship program that supports internal movement and growth

Willingness to work from our Phoenix office as part of an in-person teamComfortable using CRM systems, customer data, AI, and automation as part of your daily workflowAbility to learn products quickly and explain complex concepts simplyCurious, adaptable, and energized by helping build something newStrong communication skills and comfort advising small business owners and decision-makersExperience with payroll, benefits, HR, PEO, fintech, SaaS, or SMB customers is helpful but not requiredCommercial instinct-you recognize buying signals, can handle objections, and are comfortable asking for the businessBias toward action and a willingness to work alongside customers to solve problems and keep them movingExperience in a quota-carrying sales or other customer-facing commercial role; experience in high-velocity SMB, inbound, digital, or product-led sales is especially relevantDemonstrated ability to understand customer needs and translate them into a clear recommendationStrong organization and follow-through in a fast-moving environment