Enterprise Sales Engineer - Strategic, Financial Services
Sierra · San Francisco, CA
- Base
- $305K–$315K
- OTE
- Not disclosed
- Posted
- 3d ago
Still open · checked just nowon Sierra's careers page
What Sierra sells
AI agents that answer order and billing questions
A shopper wants to know where an order is, and a bank customer needs a new card fast. Sierra builds AI agents that handle these customer questions for businesses, from order tracking to billing support, tuned to each company's own voice. Customers get their answers from an agent built for the business they are dealing with.
In plain English, from their own job posts. Something wrong? Tell us
More Customer support companies →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
- Says nothing about quota, attainment, deal size, territory or sales cycle.
- Pipeline
- Mostly inbound or an assigned book.
- Time on market
- Open 3 days.
- Company hiring
- Ramping up: posted 18 sales roles in the last 30 days. That many open roles can also mean churn. Ask how many reps are still there from last year.
Red flags
None spotted.
Worth asking about
- Same role posted many times. The company has 8 or more open postings with this exact title. Could be a big build-out, could be a revolving door. Ask how many reps they hired last year and how many are still there.
Green flags
- SDR or inbound support. You won't be building all of your own pipeline from zero.
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.
How many reps are you hiring for this, and how many from last year's class are still here?
Hiring a lot can mean growth, or people leaving.
- 2.
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.
- 3.
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.
- 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.
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 Sierra? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh
The role
Technical pre-sales for Sierra's AI customer-service agent platform, covering a few large financial services accounts. You scope use cases, lead demos and architecture reviews, and stay on through launch and expansion.
Strategic · Mixed · Inbound
Selling motion
Who you're selling to
- Buyer:
- C-suite, enterprise architects, engineering and security teamsIn their words: “Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams”
- Industry:
- Financial servicesIn their words: “Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software”
- Company size:
- Strategic
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.