Braun Board

Enterprise Sales Engineer - Strategic, Retail

Sierra · San Francisco, CA

Base
$305K–$315K
OTE
Not disclosed
Posted
9d ago

Still open · checked 2h agoon Sierra's careers page

What Sierra sells

AI agents that answer customer questions for brands

When a company gets thousands of customer questions about orders, bills, or lost cards, someone has to answer each one. The problem is, people can only answer so many at once, and the questions keep coming. Sierra builds AI agents that handle order tracking and billing questions in each company's own voice, so customers get answers faster.

In plain English, from their own job posts. Something wrong? Tell us

More Customer support companies →

The Braun Read

Worth a look

Solid 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 9 days.
Company hiring
Ramping up: posted 22 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 lights

None spotted.

Yellow lights

  • 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 lights

  • SDR or inbound support. You won't be building all of your own pipeline from zero.

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. 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. 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. 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. 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. 5.

    How long is ramp, and what's the quota during it?

    Full quota on day one means you start behind.

  6. 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. 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. 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. 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 →

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The role

Technical pre-sales lead for Sierra's AI customer-facing agents at large retail brands. You scope use cases, design and demo the platform, lead architecture reviews, and stay on accounts through launch and expansion.

Strategic · Mixed · Inbound

Selling motion

Mixed

Who you're selling to

Buyer:
RetailersIn their words: “Sierra is partnering with a large and growing number of retailers”
Industry:
RetailIn their words: “ABOUT THE RETAIL TEAM”
Company size:
Strategic

Pipeline expectations

Mostly inbound or an assigned book of business.

Compensation

$305K–$315K base

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.

Full posting
ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
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