About this role.
Bundle is hiring a full-time remote Account Executive based in the Philippines to become its second sales hire. The role focuses on building greenfield outbound pipeline and owning the complete sales cycle, from cold prospecting through negotiation and close. The ideal candidate has at least two years of self-sourced closing experience, success selling to HR, People, or L&D buyers, and startup experience. The position works closely with the founder, CEO, and Head of Sales, while carrying activity, pipeline, and quarterly quota expectations.
Role DNA
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Job Complexity
4/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Account Executive role at Bundle. I bring full-cycle sales experience with a strong focus on self-sourced pipeline, cold outreach, discovery, and new-logo acquisition in developing markets.
I am particularly drawn to the opportunity to build a greenfield outbound motion alongside Bundle’s founder and sales leadership. My experience using CRM data, account-based prospecting, and consultative selling would enable me to create repeatable pipeline and help exceed quarterly goals.
I would welcome the opportunity to discuss how I can help Bundle expand its leadership-development customer base.
Sample interview questions
I would explain my prior pipeline by source, including the percentage I created independently, the channels used, conversion rates by stage, and the revenue or quota attainment that resulted. I would also describe the prospecting cadence and account-selection criteria that made the motion repeatable.
I would begin with a focused account list, identify likely CHRO, CPO, and L&D stakeholders, and tailor outreach around a specific leadership or performance-management challenge. I would use coordinated calls, email, and LinkedIn touches, then refine messaging based on response and meeting-conversion data.
I would use discovery to quantify the business impact of the customer’s management or leadership gap, map decision-makers and buying criteria, and confirm next steps with mutual action plans. I would keep CRM records current, address objections directly, and involve executive sponsors when this would advance a complex deal.
I would review activity, connection, meeting, opportunity, and stage-conversion metrics weekly to locate bottlenecks. If a metric lagged, I would test changes to targeting, messaging, channel mix, or follow-up timing while maintaining a consistent daily prospecting cadence.
I would prioritize early learning: understanding the validated playbook, speaking with customers and leadership, and quickly launching a measurable outbound cadence. I would share field feedback constructively, document what works, and help turn successful experiments into repeatable processes for future hires.
About Frontier
Frontier is a subsidiary of Fresh Prints. Fresh Prints is a New York-based, fast-growing, fully remote, 150-person company with most of our team based in India and the Philippines. A few years ago, Fresh Prints began helping other fast-growing companies build their teams. We got so good at it that we spun out a new company to focus exclusively on that — and called it Frontier.
At Frontier, we help companies grow full-time, cross-functional teams abroad. We hire the smartest people and place them into the best companies. In three years, we’ve never lost a client. If you’re interested in a Frontier role and you apply and are accepted, we’ll screen you through a couple of internal interviews and aim to get you an interview for a full-time job within the month.
Think of us as your personal talent agent — and good luck with the application! 😊
About Bundle
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.
Role Overview
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.
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.
- 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.
What You Bring
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.
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.
Why Join Bundle?
- 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
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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