via Ashby
$110K - 125K a year
Lead and architect the Customer Success organization by designing operations, driving proactive engagement, managing team performance, and collaborating cross-functionally to improve customer adoption and retention.
3+ years in post-sale customer-facing roles, 2+ years managing CSMs, experience with customer success platforms and driving retention and cross-sell targets, strong operational and data-driven skills, and leadership capabilities.
About Buildout Buildout is a family of CRE software products that help the best brokers to find, win, market, and transact properties to maximize their deal efforts and maximize wins. Our core belief is that successful commercial real estate is broker-led, but tech-enabled. That we play a critical role in maximizing the brokers time to focus on what they do best. As a result, Buildout has become the not-so-secret weapon for more than 150,000+ brokers and investors. Ultimately, we exist to serve the entire CRE industry and because of that unwavering focus, all the best brokers use Buildout. Learn more about who we are, what we do, and why we’re changing the face of CRE tech on our website: https://buildout.com/. The Opportunity We are seeking an entrepreneurial Director of Customer Success to lead and architect our Customer Success organization. This is a critical leadership role that requires a blend of strategic platform expertise, operational rigor, content creation prowess, and cross-functional leadership. You will be responsible for defining the customer journey, leveraging technology to drive proactive engagement, and ultimately, meaningfully improving customer adoption and retention for our flagship products. How You’ll Contribute at Buildout Designing & Optimizing Operations Leveraging our CS platform, Planhat, design and build automated triggers and playbooks based on activity (e.g. usage data, NPS scores, customer sentiment) to identify early warning signs, drive adoption, improve retention, and surface opportunities for cross-sell Manage CS Operations Specialist to ensure technical build-out, data integrity, reporting, and maintenance within the CS platform are executed flawlessly Collaborate with cross-functional leaders (Account Management, Billing, Implementation, Support) to solidify "swim lanes" and rules of engagement to ensure a unified customer communication experience with seamless hand-offs that feel like magic to the customer Proactive Engagement & Product Enablement Lead the strategy and support the creation of proactive, educational content (e.g., webinars, training videos, LMS courses) Manage Customer Success Manager(s), whose responsibilities focus on getting on the phone with customers to train, answer questions, and enable them to integrate the product seamlessly into their day-to-day Team Performance & Reporting Own critical company retention KPIs and drive lead generation for our sales and account management organizations Define, track, and report on key metrics and outcomes, producing senior leadership visibility into the success of our efforts Develop the KPIs and quarterly goals for your team, aligning initiatives with company goals, prioritizing and clearly articulating what will be deferred or deprioritized, and ensure resources are always aimed at the highest value work Recruit, coach, and performance manage a growing Customer Success team, including a Customer Success Operations Specialist and customer-facing Customer Success Manager(s), ensuring the team is highly skilled and effective Competencies Operationally and process minded - you are keen on having established processes and steps in place in order to achieve a desired end goal Technically savvy - you love leveraging, designing, and building technology and systems to get work done effectively and efficiently, and you fearlessly seek ways to use AI Data driven - you eat data for breakfast. You use metrics, facts, and quantitative analysis rather than intuition or anecdote to inform strategies, make decisions, and measure progress toward established goals Customer focus - you understand customer needs and are devoted to creating positive, helpful experiences Directs work - you provide direction and delegation and remove obstacles so your team can get work done Communicates effectively - you’re great on the phone and with the written word, meet the customer where they are, and are unafraid to insert some delight and levity into the day-to-day Innovative - you love tinkering and experimenting in a fast-changing environment, learning lessons and relying on data and results to inform quick iterating Drives results - you focus and prioritize the work that will impact business outcomes, and are allergic to not hitting your goals What You’ll Bring to Buildout 3+ years of experience in post-sale, customer-facing roles 2+ years of experience managing CSMs or similar post-sale customer-facing roles Experience designing and building triggers and playbooks in a customer success platform such as Planhat, Gainsight, ChurnZero Proven ability to drive results, with a track record of hitting retention and cross-sell referral targets We know there are great candidates who won’t check all of these boxes, and we also know you might bring important skills that we haven’t considered. If that’s you, don’t hesitate to apply and tell us about yourself. Location: We are HQ’d in Chicago, but operate remotely. As such, this is a remote role open across most of the US. Compensation: The targeted compensation range for this position is $110,000 - $125,000 base salary and participation in our company bonus pool. Reporting To: Elisabeth Blaha, VP of Customer Experience Perks & Benefits This program includes: Impactful insurance and benefit options, including 100% coverage of employee dental and vision insurance premiums, HSA seed, company-paid STD, LTD, life insurance, and telemedicine, and a wellness benefit of $400/year. Policies that support a healthy work/life harmony, including Flexible PTO, 14 paid company holidays, paid parental leave, and give back days 401(k) with 4% company match and immediate vesting A fully remote work culture with a monthly remote work reimbursement ($600/year) to support our distributed team and an annual, in-person company kickoff Challenging problems to solve with a committed and supportive team who are invested in your growth and development A wonderfully quirky culture where you’re encouraged to bring your whole self to work Buildout is proud to be an Equal Opportunity Employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, marital status, order of protection status, citizenship status, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. If you need a reasonable accommodation for any part of the employment process, please contact us by email at accommodations@buildout.com and let us know the nature of your request and your contact information and we will consider your request. Below, you will be asked to complete identity information for the Equal Employment Opportunity Commission (EEOC). It is required by law that we ask these questions using the format provided by the EEOC. However, we want you to know that at Buildout, we understand that gender is not binary and welcome people of all identities. For more information about our privacy practices please visit our Privacy Policy. By submitting your application, California residents consent to Buildout processing your personal information for the purpose of assessing your candidacy for this position in accordance of our Privacy Notice for Prospective California Employees.
This job posting was last updated on 12/4/2025