Sales Development Representative

About Wisewire

At Wisewire, we believe learning should be designed with intention, not intuition.

We partner with K–12 schools, workforce organizations, colleges, universities, associations, nonprofits, and employers to build engaging learning experiences that help people gain skills and achieve measurable outcomes. Our team combines learning science, instructional strategy, technology, AI-powered workflows, and human-centered design to create modern educational products that work in the real world.

We’re looking for an SDR who can introduce that work to the right people, start meaningful conversations, and turn interest into qualified opportunities.

About the Role

Wisewire is looking for a hands-on Sales Development Representative who is comfortable picking up the phone, asking good questions, and following through. You’ll build pipeline through cold calling, personalized email, HubSpot sequences, and LinkedIn outreach across education and workforce-focused markets.

Cold calling is a core part of this role. You’ll reach new prospects, reconnect with previously engaged contacts, uncover needs, and book qualified discovery meetings for our Account Executives. We need someone who can keep outreach moving consistently while making each conversation relevant.

This is a fully remote contract role for someone who takes ownership of their outreach, keeps clear records, and uses feedback and results to improve.

What You’ll Do

Build a Targeted Pipeline

• Research target organizations and decision-makers, understand their priorities, and identify where Wisewire’s learning solutions may be a fit.
• Build and maintain accurate prospect lists aligned with campaign goals and priority markets.
• Follow up with new leads and previously engaged contacts to identify current needs and opportunities.

Make Calls & Execute Multichannel Outreach

• Make consistent outbound cold calls to introduce Wisewire, start conversations, and secure relevant next steps.
• Ask focused questions, handle initial objections, and adapt your approach to the person and organization you’re contacting.
• Write concise, personalized emails and execute HubSpot sequences that support your calling and LinkedIn outreach.
• Manage follow-up thoughtfully and consistently, balancing outreach volume with quality.

Qualify Opportunities & Support the Sales Handoff

• Assess fit, understand needs and timing, and distinguish a qualified opportunity from general interest.
• Book discovery meetings for Account Executives and provide useful context, qualification notes, and agreed next steps.
• Partner with the sales team to improve messaging and meeting quality. Candidates with relevant experience may also lead initial discovery conversations.

Own CRM Accuracy & Improve Results

• Keep HubSpot current with contact information, outreach activity, call outcomes, qualification notes, and follow-up tasks.
• Track activity, responses, meetings booked, and meeting quality; share progress and identify where outreach is getting stuck.
• Test messaging and outreach approaches, apply coaching, and adjust campaigns based on what produces useful sales conversations.

Required Qualifications

• 2+ years of experience in an SDR, BDR, or outbound sales role, including hands-on cold calling.
• A demonstrated track record of generating qualified meetings through targeted outreach and consistent follow-up.
• Confidence starting cold conversations, explaining value clearly, asking useful questions, and handling objections without relying on a rigid script.
• Experience with email campaigns, outbound sequences, and a CRM or sales engagement platform.
• Strong written and verbal communication: clear, concise, professional, and attentive to the prospect’s needs.
• Ability to organize outreach independently, meet agreed activity goals, and maintain accurate CRM records in a remote environment.

Preferred Qualifications

• Hands-on experience with HubSpot CRM and sequences.
• Experience selling services or solutions in education, workforce development, or related B2B markets.
• Experience leading discovery or qualification calls and preparing clear sales handoffs.
• Experience using sales research, automation, or AI tools thoughtfully to improve outreach efficiency while reviewing messaging for accuracy and relevance.

You’ll Probably Enjoy This Role If You…

• Like starting conversations and learning what matters to the person on the other end.
• Stay consistent through unanswered calls and rejection, and learn from the conversations you do have.
• Take ownership of follow-up and prefer clear next steps over a list of contacts with no movement.
• Are curious, coachable, and motivated by building a useful pipeline.

Role Details

Engagement Type: Contract

Location: Fully remote