This position will be an on-site role out of our Tampa, FL location.
How you will contribute
The Digital Sales Ramp Coach helps new sellers turn training into confident, consistent performance in live customer conversations. This role provides hands-on coaching during the transition from onboarding to the Digital Sales team, reinforces Asure's sales methodology and processes, and partners with Sales Managers and Learning & Enablement to assess readiness. The ideal candidate brings strong consultative selling skills, an encouraging coaching style, and the ability to turn call observations and performance data into clear next steps.
Major Duties and Responsibilities
New Hire Coaching & Floor Support:
- Guide new sellers through coached live selling following initial onboarding, with daily access to feedback and support.
- Listen to live calls and recordings; 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.
Sales Readiness & Transition:
- Maintain an individual readiness scorecard covering sales skills, product and process knowledge, CRM accuracy, and independent execution.
- Review progress with each seller and their Sales Manager; recommend when the seller is ready to transition to their assigned team.
- Create focused improvement plans for sellers who need additional practice and coordinate continued support after transition.
Performance & Partnership:
- 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 the onboarding experience.
- 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.
Required Qualifications
- Demonstrated success in consultative, quota-driven sales, preferably in B2B SaaS, HCM, payroll, HR technology, or a related field.
- Experience coaching, mentoring, onboarding, or developing salespeople preferred.
- Ability to observe a sales conversation, identify a specific behavior to improve, and give 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.
- Knowledge of virtual selling tools such as Salesforce, SalesLoft, Gong, Teams, or comparable platforms preferred.
- Energetic, adaptable, organized, and motivated to help others grow in a fast-paced environment.
- Bachelor's degree preferred; demonstrated sales results and coaching ability are valued.
Compensation
The on target earning (OTE) for this position is $135,000 - $145,000, based on relevant experience, skills, and industry knowledge. Asure Software offers a variety of employee benefits. Salary information is determined by market location and is provided in accordance with state and local pay-transparency laws. Applicants should apply via www.asuresoftware.com/careers.
Benefits
- Medical, Dental, Vision, HSA, FSA- All effective on day 1!
- Company paid Basic Life Insurance, A+D, Long-Term Disability, and Short-Term Disability
- 401K Program with 3% safe harbor contribution
- Employee Stock Purchase Program
- Fitness Reimbursement Program
- Self-Managed PTO
