This position will be an on-site role out of our Tampa, FL location.
How you will contribute
Digital Sales Manager leads, coaches, and develops a team of Digital Sales Associates responsible for generating new business, expanding existing customer relationships, and driving revenue growth across Asure's portfolio. This leader creates a high-performance, high-accountability culture while guiding the team through inbound and outbound prospecting, consultative selling, product demonstrations, account management, pipeline development, and closing. The ideal candidate is a proven sales leader who combines strong business acumen, analytical discipline, and a passion for developing people with a deep commitment to the customer experience.
Major Duties and Responsibilities
- Attract, hire, onboard, coach, and retain a high-performing team of Digital Sales Associates.
- Establish a high-performance, high-accountability culture that consistently meets or exceeds monthly, quarterly, and annual sales targets.
- Provide hands-on coaching across the full digital sales cycle, including territory and account planning, outbound prospecting, discovery, consultative selling, virtual product demonstrations, proposal development, negotiation, and closing.
- Guide the team in developing opportunities from curated lists, self-generated prospects, inbound inquiries, referrals, channel partners, reseller partners, and business development activities.
- Participate in prospect and customer calls, review recorded calls, and provide deal strategy and closing support tailored to each Digital Sales Associate.
- Ensure the team conducts effective discovery, communicates value propositions and return on investment, recommends solutions aligned to customer objectives, and serves as a trusted advisor across assigned product offerings.
- Build a customer-focused sales motion that strengthens relationships with prospects, existing clients, referral sources, and business partners while identifying upsell, cross-sell, and account expansion opportunities.
- Develop, own, and monitor key performance indicators for activity, conversion, pipeline coverage, revenue, and forecast accuracy; use data to identify gaps and improve team execution.
- Maintain a deep understanding of active opportunities and business trends and provide timely, accurate forecasts and performance updates to senior management.
- Drive consistent adoption and accurate use of sales technology, including Salesforce, SalesLoft, LinkedIn Navigator, HubSpot/Pardot, Gong, virtual meeting platforms, or similar tools for activity management, pipeline progression, forecasting, and customer engagement.
- Maintain current knowledge of Asure products, services, market trends, and competitive solutions, and ensure the team develops strong product and industry expertise.
- Collaborate with Customer Success, Marketing, Support, Operations, and other internal partners to improve customer experience and support revenue growth.
Required Qualifications
- Bachelor's degree preferred; equivalent demonstrated experience, leadership ability, and business results will be considered.
- At least 2 years of experience leading or managing an inside, digital, or virtual sales team.
- At least 3 years of successful quota-carrying sales experience, preferably in SaaS, HCM, HR technology, recruiting technology, payroll, or another consultative technology sales environment.
- Demonstrated record of meeting or exceeding sales goals as both a people leader and an individual contributor.
- Strong knowledge of digital sales practices, including outbound prospecting, inbound lead management, discovery, virtual demonstrations, pipeline management, negotiation, closing, and account expansion.
- Proven ability to coach, motivate, and develop sales professionals while setting clear expectations and holding the team accountable for results.
- Analytical mindset with the ability to translate activity, conversion, pipeline, and forecast data into practical action plans.
- Experience with Salesforce or a comparable CRM and with digital selling tools such as SalesLoft, Outreach, LinkedIn Navigator, HubSpot/Pardot, Gong, Teams, Zoom, or GoToMeeting.
- Excellent verbal, written, listening, presentation, relationship-building, and problem-solving skills.
- Credibility and professionalism with direct reports, customers, candidates, cross-functional partners, and senior management.
- Results-oriented, customer-focused, adaptable, organized, and able to manage multiple priorities in a fast-paced environment.
Compensation
The on target earning (OTE) for this position is $168,000-$183,000, 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
