Strategic Solutions Engineer, Enterprise (Chicago)
ClickUp · Hybrid · Chicago, IL
- Base
- $175K–$225K
- OTE
- Not disclosed
- Posted
- 4d ago
Still open · checked 3h agoon ClickUp's careers page
What ClickUp sells
All your work tools in one place
Large companies often run their work across many separate tools, so tasks, docs, chat, and calendars end up scattered. ClickUp brings them together in one place, with AI that uses context to help. Teams can plan, talk, and get work done without jumping between apps.
In plain English, from their own job posts. Something wrong? Tell us
More Collaboration & productivity companies →The Braun Read
Ask hard questionsToo much is left unsaid. Make them answer before you invest.
- 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.
- Pipeline
- Doesn't say where pipeline comes from. Ask.
- Time on market
- Open 3 days.
- Company hiring
- 4 sales roles open, hiring at a steady pace.
Based only on what the posting says. Flags 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'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.
- 3.
Who's the economic buyer, and who else is in the deal?
Selling to a CFO and selling to a developer are different jobs.
- 4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
- 5.
Where does pipeline come from: inbound, SDRs, or me?
Tells you how much of your week is prospecting versus selling.
- 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.
Got an offer from ClickUp? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
The role
Technical pre-sales partner to Sales and Success at ClickUp. Runs proof-of-value projects, technical presentations, custom dashboards and RFP support for net-new and expansion enterprise accounts in the North East.
Strategic · Mixed
Selling motion
Who you're selling to
- Buyer:
- Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”
- Company size:
- Enterprise
Pipeline expectations
Compensation
What is not disclosed
This posting doesn't tell you:
- OTE
- Quota size
- Quota attainment
- Average deal size
- Sales cycle length
The questions above cover the big ones.