Digital Sales Coach

Asure Software • Tampa, FL

8d • Onsite

About The Position

Asure is seeking a Digital Sales Coach to help new sellers translate training into confident, consistent performance in live customer conversations. The coach provides hands-on support as sellers move from onboarding to the Digital Sales team, reinforces Asure’s sales methodology and processes, and works with Sales Managers and Learning & Enablement to assess readiness. The role calls for consultative selling ability, an encouraging coaching style, and skill in turning call observations and performance data into clear next steps.

This is an on-site position based in Tampa, Florida. The coach guides new sellers through coached live selling, listens to live calls and recordings, provides specific feedback, and leads role plays, practice sessions, call reviews, and skill-building huddles. The coach also maintains readiness scorecards, coordinates improvement plans and post-transition support, monitors early performance indicators, and reinforces accurate use of sales tools.

Asure Software offers employee benefits including medical, dental, and vision coverage; HSA and FSA; company-paid basic life insurance, AD&D, long- and short-term disability; a 401(k) program with a 3% safe harbor contribution; an employee stock purchase program; fitness reimbursement; and self-managed PTO. The stated on-target earnings are $135,000–$145,000, based on relevant experience, skills, and industry knowledge.

Requirements

• Demonstrated success in consultative, quota-driven sales.
• Ability to observe a sales conversation, identify a specific behavior to improve, and provide clear, constructive feedback.
• Strong facilitation, communication, relationship-building, and problem-solving skills.
• Comfort working with call recordings, CRM data, and performance measures to guide coaching.
• Energetic, adaptable, organized, and motivated to help others grow in a fast-paced environment.
• All candidates must be legally authorized to work in the United States; the company is unable to sponsor or transfer visas.

Nice To Haves

• Sales experience in B2B SaaS, HCM, payroll, HR technology, or a related field.
• Experience coaching, mentoring, onboarding, or developing salespeople.
• Knowledge of virtual selling tools such as Salesforce, SalesLoft, Gong, Teams, or comparable platforms.
• Bachelor’s degree; demonstrated sales results and coaching ability are also valued.

Responsibilities

• Guide new sellers through coached live selling after initial onboarding, with daily access to feedback and support.
• Listen to live calls and recordings and provide specific feedback on discovery, solution fit, value, objections, next steps, and follow-up.
• Lead role plays, practice sessions, call reviews, and short skill-building huddles based on observed needs.
• Model effective customer conversations and help sellers build confidence while maintaining a strong customer experience.
• Maintain an individual readiness scorecard covering sales skills, product and process knowledge, CRM accuracy, and independent execution.
• Review seller progress with each seller and their Sales Manager, and recommend when the seller is ready to transition to their assigned team.
• Create focused improvement plans for sellers needing additional practice and coordinate continued support after transition.
• Track coaching activity and early indicators of seller progress, including call quality, pipeline creation, conversion, and time to readiness.
• Partner with Sales Managers and Learning & Enablement to reinforce training, share recurring skill gaps, and improve onboarding.
• Reinforce accurate use of Salesforce, SalesLoft, Gong, and other assigned sales tools.
• Support ongoing skill development for sellers as business needs and coaching capacity allow.

Benefits

• Medical, dental, and vision coverage, plus HSA and FSA; effective on day one.
• Company-paid basic life insurance, AD&D, long-term disability, and short-term disability.
• 401(k) program with a 3% safe harbor contribution.
• Employee stock purchase program.
• Fitness reimbursement program.
• Self-managed PTO.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed