Braun Board

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

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The Braun Read

Ask hard questions

Too 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. 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. 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. 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. 4.

    Where does pipeline come from: inbound, SDRs, or me?

    Tells you how much of your week is prospecting versus selling.

  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.

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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

Not stated in the posting.

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

Not stated in the posting.

Compensation

$185K–$203K 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
We’re building the AI-driven future of customer success, from retention to growth! We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link https://www.gainsight.com. About This Role: We’re looking for a full-time Senior Manager, Office of the CSO to join our Security team reporting to the Chief Security Officer. This role is a remote role based in the USA. In this role, you'll play a key role in building Gainsight's security trusted-advisor function by supporting enterprise sales engagements, articulating Gainsight's security posture to CISOs, CIOs, and executives, and building out the program alongside the Chief Security Officer. This is a great opportunity for someone who thrives in a fast-growing, cloud-first environment and enjoys working cross-functionally with teams like GTM, Engineering, and Security. The ideal candidate brings strong skills in security operations and engineering, enterprise sales enablement, and executive communication and storytelling. What You'll Do: - Support GTM and Customer Service for all security concerns with our prospects, customers and partners - Build out the success criteria for supporting the business - Work closely with engineering and security to help define the product roadmap based on customer needs. - Attract, mentor, and retain a world-class team of security strategists. Foster a culture of excellence, innovation, and continuous learning to meet the evolving needs of the organization   This role may require occasional travel (up to 10-20%) for team meetings, training, or company events. This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. What We're Looking For: - 5+ years of Security Leadership - 7+ years of experience with compliance, security engineering and application security - Proven experience supporting enterprise sales cycles or acting in a customer-facing advisory role. - Ability to communicate effectively with both technical and non-technical executive audiences. - Strong presentation, storytelling, and influencing skills. Nice-to-have skills or experience: - Experience managing a security team supporting GTM - Experience developing whitepapers, and point-of-view content on modern security architectures and trends. - Security Certifications (CISSP, CISA, CISM etc.) Why You’ll Love It Here: Gainsight is a place where innovation is shaped through collaboration, curiosity, and a shared focus on solving real-world problems. With a growing suite of products across customer success, product experience, community, education, and AI-powered relationship intelligence, we continue to evolve with the needs of our customers. When people with diverse strengths, a strong sense of community, and true passion for our mission come together, they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability, trust, and support that people need - not just to do the job, but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons. Here are a few: Our Compensation and Benefits: At Gainsight, we believe great work happens when teammates feel fully supported. - The starting base salary range for this role is $185,000 - $202,800 USD annually. Actual compensation may vary based on factors such as skills, experience, and location. In addition to base pay, this role is eligible for an annual bonus and participation in Gainsight’s equity program. - We offer a comprehensive benefits package including fully covered medical premiums (employee-only), flexible PTO, 401(k) plan, dental and vision coverage, and remote work options. Additional benefits include a $10,000 lifetime fertility stipend and access to coworking spaces around the globe. You'll also enjoy dedicated Recharge Holidays - one long weekend each quarter to relax and reset. Our Core Values: We are guided by our values and our mission to be living proof you can win in business while being Human-First. Learn more here https://www.gainsight.com/company/.   Our Growth Opportunities: From mentoring to career development opportunities, we’re passionate about helping our teammates learn, grow, and thrive.   Our Parody Videos: No explanation needed. Just watch them here! https://www.youtube.com/playlist?list=PLB2Z_xLbXPiAcvQr28ggP2CndoSu29zq_   If this sounds like the right role for you, we’d love to hear from you.   Additional Information: We’re committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates. If you require accommodations or have questions about how your personal data will be used during the hiring process, please contact recruiting@gainsight.com. If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.
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