Founding Sales Development Representative (SDR)

BusPlanner · Remote · US

Base: Not disclosed
OTE: Not disclosed
Quota attainment: Not disclosed
Posted: 2mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 1h agoon BusPlanner's careers page

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The job

What you'd do: Generate outbound pipeline by cold calling, emailing, and LinkedIn-prospecting US K-12 school districts, then qualify and hand off opportunities to Account Executives. Sells BusPlanner transportation software.
Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Pipeline: Mostly self-sourced. Great if you like outbound, rough if you don't.
Time on market: Open 69 days. Ask why it's been hard to fill.
Company hiring: 2 sales roles open, hiring at a steady pace.

Red lights

None spotted.

Green lights

Clear path to promotion. The posting spells out a path to the next role, like SDR to AE. Ask how long it took the last few people and what they had to hit.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
3.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
4.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
5.
What are the base and the OTE for this role?
No point investing hours before you know the number.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

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Full posting

BusPlanner is looking for a Founding Sales Development Representative (SDR) to join our fast-growing Sales team. This is not a typical SDR role; it’s a ground-floor opportunity to build our outbound engine from scratch and fast-track into an Account Executive role within 6–9 months for the right performer. Your mandate is to generate pipeline, qualify opportunities, and open doors across US school districts. You’ll operate as the tip of the spear, creating opportunities that accelerate BusPlanner’s growth in key markets. This role is perfect for someone who is hungry, entrepreneurial, and wants to prove themselves quickly and move up fast. You’ll work directly with Sales leadership and gain visibility across the entire company. This is a remote role and may include occasional travel. Why BusPlanner? BusPlanner is a leading North American tech company that provides all-in-one transportation management software to K-12 school districts. Across our customer base, we enable hundreds of transportation directors to save thousands of dollars every year by running all facets of their operations entirely through our intuitive, and easy-to-use platform. BusPlanner’s product suite is embedded across the majority of school districts in Canada and is currently making significant inroads in the US market, having won contracts with some of the largest school districts in the country including Miami-Dade (Florida), Prince George's (Maryland), Guilford (North Carolina), as well as many others. BusPlanner has a history of serving the education market and is favorably positioned to further penetrate the US market in the coming years. BusPlanner’s leadership team consists of seasoned entrepreneurs who have significant experience in building and growing multiple successful software businesses including: (i) FieldEdge, a leading provider of software for the field services market which the team grew more than 5x and sold to a mega-cap private equity fund, and (ii) AutoLeap, a leader in the auto repair software market that has raised more than $50 million from some of the most reputable VC firms in Silicon Valley. Requirements As a successful Founding SDR, you will: - Own top-of-funnel pipeline generation through cold calling, emailing, LinkedIn outreach, and creative outbound tactics. - Qualify inbound and outbound opportunities and partner closely with Account Executives for smooth handoffs. - Run targeted outbound campaigns to penetrate high-value school districts across the U.S. - Experiment aggressively to refine messaging, test sequence strategies, and improve conversion. - Collaborate with Sales leadership on outbound approach, territory strategy, and account prioritization. - Help shape our sales systems, including CRM structure, Outreach sequences, enrichment workflows, and reporting. - Represent BusPlanner at conferences to support onsite prospecting and pipeline creation. - Advance quickly: strong performers have a defined 6–9 month path to an AE role, with mentorship and support to get there. To be successful in this role, you will need: - Extreme drive and grit: You love outbound, you love the hunt, and you love creating opportunity. - Entrepreneurial mindset: Comfort in an environment where there isn’t a playbook yet (you’re helping build it). - Strong communication & questioning skills: You can capture attention and uncover pain quickly. - High organization & tech-savviness: Proficiency with CRM and sales automation tools. - Curiosity: You dig deep, ask smart questions, and constantly refine your approach. - Coachability: You’re hungry for feedback and improve fast. - Resilience: You handle rejection well and maintain high energy.

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