Customer Success Manager

About iSpeedToLead

iSpeedToLead is a two-sided real estate lead marketplace operating across the United States. Sellers of motivated-seller leads list on one side, and real estate investors buy on the other. We are a bootstrapped, profitable product company with an engineering and analytics team that ships fast and makes decisions from data rather than opinion.

About the role

This is the first dedicated Customer Success hire at iSpeedToLead. Today, buyers are supported reactively: tickets get answered, credits get issued, and nobody owns what happens to an account between its first purchase and its last one.

You will own the post-purchase relationship with our buyers. That means onboarding them properly, keeping high-value accounts healthy, and turning churn from something we observe into something we manage. You will build the function itself (playbooks, health scoring, reporting) rather than inherit it.

One thing worth stating openly before you apply: the workload is around 50 hours a week for the first 6 to 9 months while the function is being built. We would rather you decline now than discover it in month two.

Key responsibilities

Onboarding and activation

Own the onboarding of new buyers end to end, from first purchase to first repeat purchase.

Run onboarding calls and follow-ups, making sure every new buyer understands how to filter, buy, and work leads effectively.

Design and maintain the onboarding sequence (content, timing, channel) and improve it based on what actually converts.

Account health and retention

Manage a book of high-value accounts with regular check-ins, usage reviews, and proactive outreach.

Build and maintain a health-scoring model that flags at-risk accounts before they churn, not after.

Run save conversations on at-risk accounts and document what worked, by reason code.

Escalations and problem-solving

Act as the escalation point for buyer complaints, including lead quality disputes, refund requests, and billing or balance issues.

Coordinate with support, sales, and engineering to resolve issues, and follow through until the customer confirms resolution.

Operate within agreed refund and credit authority limits, and defend those decisions with data.

Voice of the customer

Collect, categorise, and quantify churn and refund reasons, turning anecdotes into a ranked list.

Deliver a weekly written report to product and leadership on retention performance and the top issues driving cancellations.

Advocate for the product changes that would remove recurring causes of churn.

Process and reporting

Build the Customer Success playbooks from scratch: onboarding, save, win-back, and escalation.

Maintain accurate account records and interaction history in our systems.

Report on retention metrics weekly, and own the definitions behind them.

Collaboration

Work daily with sales on the handoff of new buyers, and with support on ticket patterns.

Partner with product and analytics on lifecycle experiments and instrumentation.

Requirements

2+ years in Customer Success, Account Management, or Retention in a high-volume, low-ACV environment such as a marketplace, self-serve SaaS, or transactional product with hundreds of accounts. (Enterprise CSM experience with a handful of large logos is a different job and will not transfer well here.)

Demonstrated ownership of a retention, churn, or repeat-purchase metric. You can describe what it was, what you changed, and what it became.

Comfortable working with data: SQL basics or strong BI fluency (Amplitude, Metabase, Looker, BigQuery, or similar). You pull your own numbers rather than requesting them.

Experience building a process from zero, such as an onboarding flow, a save playbook, or a health-score model. Executing someone else's process is not the same thing.

Written and spoken English at C1 level, customer-facing, at volume.

Confident on the phone with US small-business customers. Our buyers are real estate investors: direct, busy, and blunt.

Practical use of AI tools in your daily workflow (call summarisation, drafting, triage) with examples you can show.

A minimum of 4 hours of daily overlap with US Eastern Time.

Nice to have

Experience in real estate, proptech, lead generation, or a marketplace with wallet or prepaid-balance mechanics.

Familiarity with Intercom, HubSpot, or a comparable CRM and support stack.

Experience designing lifecycle email or automation flows.

Ukrainian or Russian in addition to English.

What we offer

Full ownership of a metric that shows up directly in the P&L, with no layer between you and leadership.

A greenfield function. You design how Customer Success works here.

Real data infrastructure and an AI-native team, so arguments get settled with numbers and tooling is not a fight.

A clear 12-month growth path to Head of Retention or Head of Customer Success, including automation of the low-touch tier and one to two direct reports.

Remote work with flexible hours inside the required US overlap.

Referral bonus of USD 3,000 after probation for anyone you bring in.