Customer Success Associate

Summary

The Customer Success Associate (CSA) is an early-career role on ClearPoint’s Customer Success team. CSAs own a portfolio of small and mid-market accounts end-to-end and partner with CSMs and CS Leadership on larger accounts. The CSA is the customer’s primary advisor for strategy execution inside ClearPoint and is expected to exercise independent judgment on how each customer should be set up, coached, and grown.
This is not a checklist role. It is a judgment role. CSAs decide what each account needs, when to push back on a customer request, when to escalate, and what to recommend at renewal. Our customers should walk away from every interaction smarter and better positioned to be the hero inside their organization. That sometimes means redirecting a request that won’t actually serve them, recommending a different scope, or holding the line on a best practice. It always means showing up as a partner who knows the work.
This is an AI-first role. CSAs work side-by-side with Agency’s Kai, our AI teammate, from day one. We expect CSAs to design AI-driven workflows for their accounts, exercise judgment over AI output, and decide when to apply it. The CSAs who succeed here will be doing the work of two or three traditional CSAs because of how they use AI.
The ideal candidate is smart, hard-working, hungry, and humble—eager to learn without an ego, motivated to own outcomes, and a genuine team player. You read the agenda before the meeting and the report after it. You ask good questions. You don’t need to be told twice.

Responsibilities

This role’s primary duty is advising ClearPoint customers on how to execute their strategy inside the platform and exercising independent judgment on the matters listed below. Specifically, the CSA will:

• Own a portfolio of small and mid-market customers end-to-end. The CSA decides how each account is structured, what the success plan looks like, when to engage, and what to recommend. The CSA is the primary point of contact and the primary decision-maker on day-to-day account strategy.
• Make renewal and expansion recommendations. The CSA assesses account health, identifies risk and expansion signals, and makes the recommendation to leadership on renewal terms, expansion opportunities, and at-risk interventions. These recommendations directly influence revenue decisions.
• Exercise judgment on customer requests. Decide when to fulfill a request, when to push back, when to redirect, and when to escalate. Customers do not always know what they need; the CSA’s job is to diagnose and advise, not to take orders.
• Advise customers on strategy execution methodology. Coach customers on Balanced Scorecard, OKR, and ClearPoint best practices. Influence how the customer organization runs its strategy process—a matter of significance to their business.
• Design and run customer working sessions when they add value. The CSA decides cadence, agenda, and approach based on account-specific judgment—not a fixed playbook.
• Partner with CSMs on Enterprise and Growth accounts by leading defined workstreams: customer research, working-session prep, customer-facing materials, and analysis. The CSA owns these workstreams and exercises judgment on approach and output.
• Drive product adoption by deciding which features matter for each account and how to position them against the customer’s goals.
• Design AI-driven workflows. Build prompts, workflows, and automations using Agency and other AI tools. Exercise judgment over AI output, catch errors, and own the final work product.
• Provide structured product feedback to Product, Sales, and Marketing as a voice of the customer.
• Contribute to internal initiatives that imp rove how the CS team operates.

​​​​​​​Outside of the primary advisory duties above, the CSA will also:

• Triage and respond to customer support tickets in coordination with the Customer Support and CSE teams. Support work is a secondary duty and is expected to represent a minority of the role.
• Run onboarding sessions for new customers, applying CSA judgment on how each customer should be set up.

This job description is not a comprehensive list of duties. Responsibilities and activities may change at any time, with or without notice—often quickly.

What Success Looks Like

We measure CSAs on outcomes, not inputs:

• Strategic Coaching. Customers see you as someone who knows the work and helps them think more clearly—not just as a software contact.
• Onboarding and Adoption. Your customers reach first value quickly and feel set up for long-term success.
• Retention and Expansion. Your renewal recommendations are sound. Your customers renew because ClearPoint is critical to their work, and they grow because you helped them see what was possible.
• Judgment Quality. The decisions you make on account strategy, escalation, and customer requests hold up over time.
• AI Leverage. You consistently demonstrate that AI is multiplying your output—your responsiveness, your depth, your reach.
• Trajectory. You’re visibly getting better month after month. The CSA role is a launchpad into CSM, CSE, and other roles across the company.

The Work Pace

This is not a 9-to-5 job. We’re also not asking anyone to work 996. The reality sits in between: this is a startup environment, things move fast, and you will not be working banker’s hours. this is a startup environment, things move fast, and CSAs are trusted to be present when it matters and to step back when it doesn’t.

What you get in exchange is the chance to shape things and make an impact from day one. Your judgment matters, your work gets seen, and you grow fast. The CSA role is a launchpad—the people who do it well move into CSM, CSE, or other roles across the company.

The Work Environment

This position is fully remote but candidates must live in the greater DC metro area (DC, MD, VA, PA).
Expectation of 2–3 days per month in-office or in-person for team events, working sessions, and customer meetings.

Living the ClearPoint Values

We hire and promote against our core values. You should be able to come to an interview with concrete examples from your current or past work and of how you have lived each of them (If those examples don’t come naturally, this probably isn’t the right seat):

• We Care About The Customer: A time you made your customer the hero, where they walked away looking smart to their organization because of how you showed up. We are partners, not vendors.
• We Play To Win: A time you held yourself or your team accountable for great work, and what you did when the bar wasn’t being met.
• We Are Passionate: A time you worked hard, got stuff done, and still made the work fun. Bonus if you can describe a culture you helped build, not just lived in.
• We Are Exceptionally Open: A time you flagged a problem early, asked the awkward question, or surfaced something uncomfortable instead of letting it sit.
• We Are Welcoming: A time you helped build an environment where people with different backgrounds or perspectives could do their best work.

Who You Are

• Hungry. You want the work. You want to learn. You want to be good at this
• Humble. You ask questions, you take feedback, and you don’t pretend to know things
• Fast. You move quickly, write clearly, and don’t need a lot of structure to make progress
• Comfortable with ambiguity . Priorities shift, processes change, and that’s okay
• Direct. You say what you think, you push back necessary, and you don’t hide bad news
• AI-fluent or AI-curious. You already use AI in your day-to-day
• Clear communicator. You write well, you listen, and you can explain things well
• Organized. You can juggle a big task list and prioritize without dropping balls
• Curious. You read. You poke at the edges. You want to understand why, not just what

Preferred Education and Experience

• Bachelor’s degree or four years of relevant experience.
• Working fluency with Microsoft Office Suite required.
• Hands-on experience using AI tools (Claude, ChatGPT, Agency, Copilot, etc) preferred.
• Previous coursework or experience in strategy or performance management preferred.
• Customer-facing experience, particularly in technology, preferred.

Base Salary Range

• $50,000 - $70,000
• Performance-based bonus program

Benefits

• Competitive salary commensurate with your experience
• Performance-based bonus program
• 100% paid health insurance & dental insurance
• 401(k) program
• Open vacation policy
• Professional development, training, and mentorship programs

Why work for ClearPoint?

• Chance to get in on the “ground floor” of a tech company with startup energy
• Ability to make a difference from day one
• Fantastic colleagues and customers
• Employee referral bonuses to encourage the addition of great new people to the team
• Team events and offsite retreats
• Company organized volunteer days

Eligibility Requirements

• Candidates must live within ~100 miles of Arlington, VA and lives in the following states: VA, DC, MD, PA.
• Employment is contingent upon successful completion of the I9 Federal work authorization verification. We don't offer visa sponsorship or work permits.
• Employment is contingent upon successful background and reference checks.

Interested?

Please read this posting carefully, visit our website, learn about us, and then apply. To be considered, please fill out the form and attach your resume. We needed someone yesterday, and we are excited to grow our team, so if you're a good fit, expect this process to move quickly.

Pre-Employment Background Checks

All offers of employment are contingent upon clear results of a thorough background check. Background checks will be conducted on all final candidates and on all employees who are promoted, as deemed necessary and may include: Social Security Verification, Criminal History, Credit History, Personal and Professional References, social media, Prior Employment Verification, Educational Verification, and Motor Vehicle Records. ClearPoint reserves the right to modify this policy at any time without notice.

EEO Statement

ClearPoint Strategy provides equal employment opportunities (EEO) to all employees and applicants without regard to race, color, religion, sex, national origin, sexual orientation, gender identity, age, disability, or genetics. We seek to build a diverse staff representative of the communities we serve. All qualified applicants are strongly encouraged to apply.

Physical Requirements

This is sedentary work requiring typing and other and repetitive motions. Vocal communication is required for expressing or exchanging ideas by means of the spoken word. Hearing is required to perceive information at normal spoken word levels. Visual acuity is required for operation of a computer and for observing general surroundings and activities. The worker is not subject to adverse environmental conditions.