[Hiring] Customer Success Manager, AI & Automation @Small Improvements

Role Description

This is a full-cycle CSM role with a long-term focus: over time, you'll own our entire AI and digital motion, as well as the systems that deliver a great customer experience even when a dedicated CSM isn't in the room.

We're a lean Customer Team of three, looking for our fourth member. Everyone runs discovery calls, manages a book of business, and supports customers. But each person also owns an internal focus area. Yours will be our AI and digital CS infrastructure, working closely with automations, workflows, and data-driven programs to scale our impact beyond what four people can do manually.

You won't be thrown into the deep end on day one. You'll ramp up over a few months, starting with customer work first, learning what actually drives success. Then you'll start building incrementally and intentionally, one small improvement at a time.

Your Day-to-Day (Primary Focus)

• Run discovery and consultative conversations with prospective customers, focused on long-term fit and outcomes, not just closing.
• Own the full customer journey from first conversation through onboarding, adoption, and renewal.
• Act as the primary partner for your book of business by building trust, driving alignment, and identifying expansion opportunities.
• Surface patterns across accounts and bring them back to the team to improve how we work and what we build.

Your Internal Project Focus (Secondary, Grows Over Time)

• As you learn the patterns that drive customer success, you'll start turning them into scalable systems.
• Build and maintain automated workflows across Vitally, HubSpot, and Intercom, connecting the three to create seamless customer experiences and reduce manual work for the team.
• Write SQL to pull and analyze data from BigQuery, surfacing the signals that help us intervene early or identify opportunities.
• Design digital CS programs that keep customers progressing, even those without a dedicated CSM, through smart, timely, personalized touchpoints.
• Turn what works in practice into repeatable assets: playbooks, automated sequences, guides, and videos.

We're Likely a Good Fit If…

• You've managed a book of business end-to-end and genuinely care about customer outcomes, not just renewal metrics.
• You've personally built automations and workflows before, not just used them. You know what it takes to connect tools and make them work together.
• You're comfortable figuring things out without an engineering team to lean on. You find workarounds, read documentation, and get things done resourcefully.
• You've worked at a small company and understand what that means: shared ownership, no defined playbooks, and a bias toward action over process.
• You're energized by building something from scratch (a digital CS motion that doesn't fully exist yet) rather than inheriting a finished system.
• You think in systems. When you solve a problem once, you immediately think about how to make it repeatable.

We're Probably Not a Good Fit If…

• You prefer strict handoffs between sales, implementation, and CS. We share ownership of the full customer journey.
• You're uncomfortable getting into technical details. Configuring tools, writing queries, and building workflows are real parts of this role. We'll help you and use AI, but you need to get your hands dirty.
• Your instinct is to ask engineering for help when something gets technically complex. Our engineering team is small and focused on the product.
• You're looking for a fully defined playbook. We're a small team that's still shaping how we work, and you'll help write the next chapter.
• You want to automate first and learn later. We build from real patterns, not assumptions.

Your Experience

• The sweet spot is someone who has done both: owned customer relationships and built technical systems. Candidates coming from Digital CS, CS Operations with customer-facing ownership, Implementation, or Technical Account Management will be the strongest fit.
• 1–2+ years in Customer Success or Account Management in B2B SaaS, with full-cycle ownership of a book of business.
• 2–3+ years of hands-on experience building automations and workflows, ideally across multiple tools. You've connected systems, not just used them.
• Comfortable working with data: pulling reports, identifying trends, and translating numbers into action. SQL experience or a willingness to learn is a plus.
• Resourceful by nature: you figure things out without waiting for someone else to do it for you.
• Experience at a small or early-stage company where you had to create structure, not just follow it.
• Familiarity with tools like Vitally, HubSpot, or Intercom is a plus, and excitement about going deep on them is a must.
• A plus: experience in HR Tech, Performance Management, or people operations software.

What Success Looks Like in 6 Months

• You've built strong relationships with your initial book of business and understand how each customer defines success.
• You're confidently running discovery calls and owning the full customer journey end-to-end.
• You've identified at least one pattern across your accounts and turned it into a scalable workflow, automation, or resource.
• You have a clear point of view on what's working, what isn't, and where the biggest opportunities are in our digital CS motion.

Compensation & Benefits

• Base salary: $70,000 – $75,000
• Location: Remote, continental U.S. Preference for candidates in or around Austin, TX, but not required.
• Health & wellness: Comprehensive Medical, Vision, and Dental coverage, plus a $1,200 annual wellness budget.
• Time off: 21 days paid vacation (increasing with tenure) plus 10 public holidays.
• Learning & development: $3,500 annual budget.
• Home office: $500 setup budget.

Hear From the Team

• 'Autonomy and collaboration are highly valued at Small Improvements. We are not just a team but a close-knit community that values each other's input. I appreciate the freedom to take ownership of my work while collaborating closely with my colleagues.' — Lindsay, VP of Customer Success, joined December 2019
• 'This team lives by its values. I'm appreciated for my individual talents and knowledge. You will be free to advocate for organizational improvements and bounce ideas off your peers. Every company says they prioritize work-life balance, but this is the real deal.' — Alec, Customer Success Manager, joined July 2024