Senior Manager, Office of the CSO
Gainsight · Remote · US
- Base
- $185K–$203K
- OTE
- Not disclosed
- Posted
- 1mo ago
Still open · checked 1h agoon Gainsight's careers page
What Gainsight sells
Keeps software customers learning, using, and staying
A software company wants its customers to stay, use the product well, and recommend it to others. Gainsight's software follows each customer from their first day through getting real results and becoming fans. AI helpers support learning, adoption, and community, so customers keep getting value.
In plain English, from their own job posts. Something wrong? Tell us
More Sales & marketing 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
- Says nothing about quota, attainment, deal size, territory or sales cycle.
- Pipeline
- Doesn't say where pipeline comes from. Ask.
- Time on market
- Open 55 days. Ask why it's been hard to fill.
- Company hiring
- This is their only open sales role.
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.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
- 4.
Where does pipeline come from: inbound, SDRs, or me?
Tells you how much of your week is prospecting versus selling.
- 5.
How long is ramp, and what's the quota during it?
Full quota on day one means you start behind.
- 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 Gainsight? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
The role
Security leadership role, not a quota-carrying sales job. Supports enterprise sales deals by advising prospects' CISOs and executives on Gainsight's security posture, alongside GTM teams.
Selling motion
Who you're selling to
- Buyer:
- CISOs and CIOsIn their words: “articulating Gainsight's security posture to CISOs, CIOs, and executives”
- Company size:
- Enterprise
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.