DigiWise Global
Lead Generation Specialist (Senior SDR) | Finance & Tax Knowledge Required
Remote
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Contractor
Company website
B2B Software | Short-Term Engagement with Potential for Direct Hire DigiWise is seeking an experienced sales professional to support a client offering AI and business software solutions. This role is a strong fit for someone who can confidently engage CPAs and business owners, generate interest, and turn outreach into qualified sales meetings. You will work directly with the client’s founder, who provides initial training, sets daily priorities, and handles demos and closing. Your focus will be outbound calling, coordinating email outreach, and maintaining consistent follow-up with prospects. The initial engagement runs through December 31, 2026, with the possibility of an extension or direct employment with the client.
About DigiWise Global
DigiWise embeds proven operators directly into client organizations, practitioners who have already held the roles they are brought in to fill. Our teams work across digital marketing, strategy and insights, systems integration, pricing and finance, and talent placement, remaining in place until the work is complete.
Description
What You’ll Do
- Conduct outbound calls using established prospect lists, prioritizing CPAs and accounting firms.
- Engage CPAs and business owners in conversations about the client’s software offerings and business finance and tax-related purchasing considerations.
- Coordinate email campaigns with DigiWise team members supporting campaign development and execution.
- Monitor LinkedIn outreach campaigns and respond to interested prospects.
- Qualify leads, follow up on open opportunities, and schedule Zoom meetings for the founder.
- Coordinate CPA participation in meetings with business owners.
- Learn and apply the founder’s messaging, qualification process, and sales approach.
- Maintain current CRM records, including outreach activity, conversation notes, lead status, and next steps.
- Report weekly on calls, conversations, meetings scheduled, and meetings held.
Required Qualifications
- At least 10 years of B2B sales experience, including software sales.
- A working understanding of business finance, taxes, and depreciation sufficient to hold credible conversations with CPAs, including how qualifying software purchases may reduce taxable income.
- A confident, consultative phone presence with CPAs and business owners, with the ability to engage beyond a scripted introduction.
- A proven record of generating qualified meetings for a closer through outbound calling and disciplined follow-up.
- The ability to learn a new offering within the first few days of training and work independently afterward.
- Strong organization, accountability, and daily CRM use for call logging, lead tracking, and reporting. Training on the client’s CRM will be provided.
Preferred Qualifications
- Financial software sales experience where CPAs or accounting firms were among the primary buyers.
- Sales engineering experience.
- Experience running or directing email and LinkedIn outreach campaigns.
- Familiarity with specific business tax strategies, including Section 179 and bonus depreciation.
Engagement Details
- Placement: Through DigiWise, supporting a client directly
- Anticipated start: Shortly after November 1, 2026
- Initial term: Through December 31, 2026
- Training and direction: Directly from the client’s founder
- Future opportunities: Potential extension or direct hire, subject to business needs and mutual agreement
- Selection process: Screening by DigiWise followed by a client interview