[Hiring] Sales Development Representative @Fresh Prints

Role Description

We’re hiring our second sales hire, and this role is built for a hunter. You will own outbound prospecting at Bundle: greenfield territory, a proven playbook built and validated by our founder, and full ownership of the pipeline you create, from first touch to booking qualified meetings.

This is not a role where leads land in your lap. Marketing generates strong inbound today, but we’re hiring you to build the other engine. The majority of your pipeline will be self-sourced through cold outreach to CHROs, CPOs, and L&D leaders at mid-market and enterprise companies. You’ll work directly with our founder and CEO and our Head of Sales, source alongside them, and shape how outbound works here for everyone who comes after you. If you’ve done the early-stage thing before and want to do it again with a company that’s already working, this is your seat.

What You’ll Do

• Build and own your pipeline. Prospect daily through cold calls, email, and LinkedIn; the majority of your opportunities should be self-sourced.
• Drive top-of-funnel engagement: identify target accounts, reach decision-makers, run discovery, and hand off qualified opportunities to senior sales leaders.
• Work from and improve our proven outbound playbook, including message templates, target lists, and pain-point-led outreach.
• Partner with marketing on shared target accounts so outbound and inbound warm the same buyers.
• Hit daily, weekly, and quarterly activity and pipeline metrics.
• Meet and exceed quarterly meeting and pipeline generation goals.
• Track and update all sales activities and contacts in the CRM.

Qualifications

• 2+ years of outbound sales or SDR experience where you sourced most of your own pipeline. Be ready to walk us through what percentage of your pipeline you personally generated and how.
• Proven success with cold outreach (calls, email, LinkedIn) and a track record of new logo acquisition in an underdeveloped or under-penetrated territory.
• Experience selling to HR, People, or L&D buyers (CHRO, CPO, Head of L&D, or similar).
• Startup experience at a company under 100 people, ideally as one of the first few salespeople, and a genuine preference for early-stage building over big-company infrastructure.
• Proven track record of meeting activity and pipeline targets.
• Independent work ethic with the ability to problem-solve; outstanding verbal and written communication skills.
• Experience with HubSpot or a comparable CRM.

Desired Requirements

• You were an early or founding sales hire somewhere before.
• Past experience at a performance management, leadership development, coaching, or L&D technology company.

Benefits

• Six straight quarters of hitting our goals, with a validated playbook waiting for you.
• Greenfield outbound territory and a direct line to the founder and CEO.
• Uncapped Commission.
• 100% remote.
• Flexible Work Schedule.