Sales Development Representative- Chicago-
Project44 · Chicago, IL
Game over? Still on their site, but open 2+ months.
New Business: you win brand-new customers.
- Base
- $45K–$65K
- 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 2h agoon Project44's careers page
The job
- What you'd do
- Answer requests from interested companies and check they're a good fit, then cold call businesses across North America to book meetings for the sales team. You'll find many of your own prospects by phone.
- What you'd sell
Real-time shipment tracking software for global supply chains
When a company moves goods around the world, the details about each shipment usually live in many separate places. The problem is, nobody can see the whole picture at once, so it's hard to act quickly when something goes wrong. project44 pulls that scattered logistics data into one real-time view, so companies can see what's happening and act on it fast.
In plain English, from their own job posts. Something wrong? Tell me · More Industry-specific software companies →
- Who you'd sell to
- Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”
- Where deals come from
- Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.
The Braun Read
Worth a lookSolid on the basics. Use the first call to fill in the gaps.
- Pay
- Base is listed but not OTE. Ask what the variable is and how many people hit it.
- Transparency
- Shares 1 of 5: quota, attainment, deal size, territory, sales cycle.
- Time on market
- Open 82 days. Ask why it's been hard to fill.
- Company hiring
- 4 sales roles open, hiring at a steady pace.
Red lights
- Time on market. Open 82 days. Ask why it's been hard to fill.
Green lights
None spotted.
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's the OTE, and what did the median rep earn last year?
Base is what you're guaranteed. OTE and the median show the upside.
- 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 →
Going for your first AE role? Get the free interview kit → 24 questions, what good and bad answers sound like, and an offer comparison sheet.