Account Executive - Sales

Bundle delivers live 1:1 leadership and manager training with expert instructors. No micro-lessons, no click-through tutorials, just real conversations that build skills people actually use. We work with enterprise and mid-market companies across manufacturing, healthcare, construction, and beyond, and we’ve hit our goals six quarters in a row. Now we’re building toward where performance management meets live leadership development.

We’re hiring our second sales hire, and this role is built for a hunter. You will own outbound 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 close. 

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, sell 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.

• →Build and own your pipeline. Prospect daily through cold calls, email, and LinkedIn; the majority of your opportunities should be self-sourced.
• →Run the full sales cycle: identify target accounts, reach decision-makers, run discovery and pitches, negotiate pricing and terms, and close. 
• →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.
• →Travel to industry conferences and events to build pipeline, booking meetings before you go and sourcing new leads on the ground.
• →Hit daily, weekly, and quarterly activity and pipeline metrics.
• →Meet and exceed quarterly sales quota.
• →Track and update all sales activities and contacts in the CRM.

• 2+ years of full-cycle closing 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 sales quota and metrics.

• Independent work ethic with the ability to problem-solve; outstanding verbal and written communication skills.

• Experience with HubSpot or a comparable CRM.

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