Digital Sales Coach

Asure Software Inc.; Tampa (FL); On-site; USD 135,000 - 145,000; Full time

Benefits offered by this job

Medical, Dental, Vision

401K with 3% safe harbor

Employee Stock Purchase Program

Paid time off

Job summary

Asure Software Inc. in Tampa, FL is seeking a Digital Sales Ramp Coach to turn onboarding into confident, consistent performance in live customer conversations.

You will coach during the transition to the Digital Sales team, reinforce Asure’s sales methodology, and partner with Sales Managers to assess readiness. The ideal candidate has strong consultative selling skills, coaching ability, and comfort with call recordings, CRM data, and performance metrics; you’ll help create focused improvement

Qualifications

• Evidence of success in consultative, quota-driven B2B SaaS sales.
• Experience coaching, onboarding, or developing salespeople.
• Ability to observe a sales conversation and give actionable feedback.
• Strong facilitation and communication skills.
• Familiarity with Salesforce, SalesLoft, Gong, and CRM data.

Responsibilities

• Coach new sellers through coached live selling with daily feedback and support.
• Listen to live calls and recordings; provide specific feedback on discovery, solution fit, objections, next steps, and follow-up.
• Lead role plays, practice sessions, call reviews, and short skill-building huddles.
• Model effective customer conversations and help sellers build confidence while maintaining a strong customer experience.
• Track readiness scorecards and review progress with sellers and managers; coordinate continued support after transition.
• Reinforce training with sales managers and enablement; ensure accurate use of tools like Salesforce and Gong.

Skills

Consultative selling

Coaching & mentoring

Onboarding

CRM data analysis

Virtual selling tools

Communication & relationship-building

Education

Bachelor’s degree

Tools

Salesforce

SalesLoft

Gong

Teams

Job description

Who we are

Over 600 employees strong, Asure sees Human Capital Management (HCM) through the lens of entrepreneurs and executives with an owner’s mentality. We help businesses develop their “Human Capital” to get to the next level, stay compliant, and allocate their time, money and technology toward growth. Our HCM platform empowers more than 80,000 clients to build great teams and better manage their people while staying compliant in an ever-changing HR legislative landscape. Asure’s HCM offering includes Payroll & Tax, HR, and Time & Attendance software and HR Services ranging from online compliance tools to a fully outsourced HR department.

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.

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

Our Mission

To provide Human Capital Management (HCM) software and services that help companies grow, while nurturing a culture of growth around us.

• Helping customers grow by getting the most from their human capital
• Helping our employees grow personally and professionally
• Growing relationships in our communities that inspire goodness
• Grow shareholder value

Our Vision

Be the most trusted Human Capital Management resource to entrepreneurs everywhere.

Our Values

Reflect who we are and what we stand for as a company.

• Embrace Change
• Lead with Integrity
• Own the Outcome
• Deliver Awesome
• Be a Good Human

We are an equal opportunity employer. All candidates must be legally authorized to work in the US, as we are unable to sponsor or transfer Visas at this time. Criminal background checks conducted at employment offer.

NOAGENCIES PLEASE

Any unsolicited resumes sent to Asure Software from a third party, such as an Agency, including unsolicited resumes sent to Asure’s mailing address, fax machine or email address, directly to employees or hiring managers will be considered Asure property. Asure will not pay a fee for any placement resulting from the receipt of an unsolicited resume.