Director, Sales Development
Smartsheet · Boston, MA
- Base
- $111K–$129K
- OTE
- Not disclosed
- Posted
- Yesterday
Still open · checked 1h agoon Smartsheet's careers page
What Smartsheet sells
Manages team work and automates repetitive tasks
Teams have a lot of work to keep track of, and much of it is slow, repeated busywork. Smartsheet helps them manage that work, automate the manual tasks, and spot useful patterns as the work grows. That frees people to spend their time on judgment, creativity, and big thinking.
In plain English, from their own job posts. Something wrong? Tell us
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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
- Says nothing about quota, attainment, deal size, territory or sales cycle.
- Pipeline
- Doesn't say where pipeline comes from. Ask.
- Time on market
- Brand new.
- Company hiring
- 15 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 Smartsheet? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
The role
Leads an SDR team that identifies, engages and qualifies prospects for Smartsheet's work management platform, through inbound and outbound pipeline. Focus is coaching, call reviews and incentives.
New Logo
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?”
Pipeline expectations
Compensation
What is not disclosed
This posting doesn't tell you:
- OTE
- Quota size
- Quota attainment
- Average deal size
- Territory
- Sales cycle length
The questions above cover the big ones.