Customer Success Manager

Overview

You're managing 30-50 accounts (mostly startups and mid-market companies) using Bolto's platform for recruiting, payroll, and HR. You're making sure they successfully implement, adopt features, don't churn, and expand as they grow. You're the main point of contact when payroll breaks, compliance questions come up, or they need help with new features. You'll also be identifying upsell opportunities when accounts grow or need additional modules.

Role Snapshot

Company Context

Stage: Seed/Early-stage (YC-backed, 15 employees)

Size: 15 people total

Growth: Scaling quickly, likely adding customers faster than CS capacity

Market Position: Early product - expect bugs, feature gaps, and process that's still being built

GTM Reality

Your Book of Business:

• 30-50 accounts (likely growing as company scales)
• Mix of early adopters (forgiving) and newer customers (higher expectations)
• Account sizes range from 20-person startups to 200-person growth companies

Support Structure: You're probably one of the first CS hires. There might be a support team for tickets, but you're the main relationship owner. Engineering might help with escalations, but there's no huge support org yet.

Expansion Motion: When accounts grow (hiring more employees) or want to add modules (e.g., they started with payroll, now want recruiting), you're driving that conversation and closing the expansion deal.

Competitive Landscape

Churn Risk Factors:

• Product bugs or missing features vs mature competitors
• Customer outgrows Bolto's capabilities
• M&A activity (customer gets acquired, forced onto parent company's systems)
• Economic downturn (company shrinks, looks to cut costs)

Why They Stay: Cost savings vs paying for multiple tools, decent product experience, strong relationship with you

What You'll Actually Do

Time Breakdown

Reactive Support (40%) | Proactive Outreach (30%) | Expansion (20%) | Internal (10%)

Key Activities

• Onboarding and implementation: When new customers sign, you're running kickoff calls, walking them through setup, importing employee data, configuring payroll settings, and getting them to first successful payroll run. This takes 2-4 weeks per customer and is high-touch. You're probably onboarding 2-4 new accounts per month.
• Reactive firefighting: Customers Slack/email you when something breaks or they can't figure out a feature. "Payroll didn't run correctly," "Compliance report is showing an error," "I can't find how to do X." You're troubleshooting, escalating to engineering if needed, and hand-holding them through solutions. Expect 10-15 of these per week.
• Proactive health monitoring: You're checking in on accounts quarterly (or monthly for larger ones). You're looking at usage data - are they actually using the recruiting module they paid for? Is payroll running smoothly? You're running business reviews, asking about upcoming hiring plans, identifying risks before they churn.
• Expansion and upsell: When a customer goes from 50 to 100 employees, their pricing tier increases. When they want to add a module, you're positioning it, scoping the implementation, and closing the deal. You're probably closing 2-4 expansion deals per quarter.
• Product feedback loop: You're the voice of the customer internally. You're reporting bugs, feature requests, and common pain points to product/engineering. At 15 people, your input actually influences the roadmap.

The Honest Reality

What's Hard

• Early product issues: The product is newer, so there will be bugs. Payroll is mission-critical - when it breaks, customers are stressed and you're catching heat. You need to stay calm and manage expectations.
• Wearing multiple hats: You're doing onboarding, support, expansion sales, product feedback, and sometimes even training. There's no specialized team for each function yet.
• High customer expectations vs small team: Customers expect enterprise-level support, but you're at a 15-person startup. You can't be available 24/7, and some issues take time to fix. You'll need to manage expectations carefully.
• Churn risk from feature gaps: You'll lose customers because Bolto doesn't have a feature that Rippling or Gusto has. It's frustrating to lose good customers to product gaps you can't control.
• Volume vs quality: As the company grows, your book will grow too. You'll struggle to maintain the same level of high-touch service with 50 accounts as you had with 20.

What Success Looks Like

• Maintaining 95%+ gross retention (logo retention)
• Driving 110-120% net revenue retention through expansions
• Onboarding new customers to successful first payroll run within 30 days
• Responding to critical issues (payroll problems) within 2 hours
• Identifying and closing 1-2 expansion opportunities per month

Who You're Working With

Primary Contacts:

• Head of People / HR Managers (day-to-day users)
• Operations / Finance team (payroll and compliance stakeholders)
• Founders/executives at smaller customers (still involved in vendor relationships)

What They Care About:

• Reliability: Payroll cannot fail. Compliance cannot break. These are table stakes.
• Responsiveness: When they have an urgent issue, they need a quick answer.
• ROI validation: Did consolidating their stack actually save time/money or are they regretting the switch?
• Growth support: As they scale, can Bolto scale with them or will they need to migrate again?

Requirements

• 2-4 years in customer success, account management, or implementation, ideally in HR tech, payroll, or B2B SaaS
• Experience managing a book of 30+ accounts simultaneously
• Comfortable with both reactive support and proactive relationship management
• Technical enough to troubleshoot software issues and explain features clearly
• Sales skills for expansion/upsell conversations (not just relationship management)
• Comfortable with ambiguity and building process on the fly
• Bonus: experience at early-stage startups or with payroll/HR software specifically