About the Opportunity

Freckle is built for operators.

We’re the modern AI enrichment platform for HubSpot and Salesforce teams. Customers like Bolt, Applause, Sleekflow, Knowify, and Optimal Workshop use Freckle’s AI agents to enrich company and contact data across the web and 50+ providers, keeping CRM records clean, complete, and activation-ready.

As more teams rely on enrichment as real infrastructure, the customer experience has to scale with the workflow. Our customers need more than a help desk. They need a technical partner who understands messy tables, real operator constraints, and what “good data” looks like in production.

We’re hiring a Customer Solutions Engineer to own that gap at Freckle: helping customers go live with the right workflows, continuously improve their tables over time, and unlock new use cases as Freckle becomes core to how they operate.

This role requires real duality: customer-facing judgment and technical sharpness. You won’t be successful here with only one.

This is an individual contributor role reporting to the Head of Operations.

Areas of Ownership

In this role, you’ll serve as the primary technical partner for the operators running Freckle day-to-day. You’ll help customers implement workflows that work in practice, troubleshoot edge cases quickly, and scale success through education and playbooks.

• Own a book of 20+ enterprise accounts from onboarding through ongoing success. Serve as their primary technical partner and identifying opportunities to expand Freckle into new teams and use cases

• Get customers live fast. Design and execute large-scale enrichment workflows, CRM cleanup projects, and API-based integrations to ensure customers launch their first production workflow within 30 days with clean, trustworthy data

• Drive ongoing engagement and adoption. Proactively introduce new enrichment providers, workflow patterns, and use cases to keep customers getting incremental value as their needs and the platform evolve

• Build the knowledge library. Develop customer-facing documentation and in-app chat resources that help operators troubleshoot issues and level up their workflows independently

• Act as the bridge between customers and the product. Surface workflow patterns, edge cases, and feature gaps to Engineering and Product to continuously improve the platform

About You

You’re technically sharp, highly customer-oriented, and you care about making data workflows work in the real world. We’re open to different paths into this role. You might come from an ops background with a technical bent or a technical background with strong customer chops. If you enjoy vibe coding as a side quest, even better.

You likely have more than a few of the following:

• 2–5 years in a customer-facing technical role supporting production workflows (Solutions Engineering, Technical Support, Customer Success, Account Management, or similar)

• Deep experience in the GTM tools operators live in daily think HubSpot, Salesforce, Vector, Instantly, HeyReach, Trigify, etc.

• Strong technical instincts for troubleshooting integrations, enrichment workflows, sync behavior, and messy real-world edge cases

• High comfort with ambiguity where you can take an unclear customer problem and drive it to a clean outcome without relying on engineering support

• Clear communication skills externally and internally, acting as a customer whisperer in the moment and a strong advocate back to Product and Eng

• Operator mindset and ownership where you don't just raise issues but own the workflow, the fix, and what "good" should look like going forward

• Process builder by default where once you solve something twice, you want to turn it into a playbook that scales

Is This Role Right for You?

We want to be transparent about what we are hiring for and what we are not. Working at an early-stage start up comes with a different set of challenges, which for the right person results in outsized early career ownership. For the wrong person, the number of hats can be too much.

This role will not be a fit for you if:

• You want a ticket-only support role without owning workflows end-to-end

• You’re only interested in leading the technical side or the customer side

• You prefer strict handoffs and process rather than building as you go

• You’re uncomfortable working in messy CRM data and operator edge cases

• You’re looking for a predictable 9–5 instead of a high-ownership environment

What we offer

We might be biased, but working at Freckle comes with some sweet benefits.

• Hybrid work from our San Francisco office (Levi’s Plaza)

• Premium health insurance plans (medical, dental, vision)

• Two company off-sites per year (prev: Calistoga, London, Bali)

• 4 weeks PTO

What’s next

Our process is designed to be thorough but efficient, with clear criteria at each stage.

Stage 1: Initial Screen (30 min, Video)

• Meet with the Head of Operations

• Discuss your background, interest in Freckle, and initial product impressions

• Overview of the role and mutual fit

Stage 2: Technical Assignment (Take-home, ~2 hours)

• Hands-on workflow design challenge using Freckle

• Design an enrichment workflow for a realistic customer scenario

• Document your approach, decisions, and recommendations

  We'll provide sample data and clear success criteria

Stage 3: Assignment Review + Deep Dive (60 min, IRL)

• Present your workflow solution to the team

• Discuss technical decisions and trade-offs

• Role play a customer troubleshooting scenario

• Meet with the Head of Growth + Head of Engineering

Stage 4: Team Fit + Ops Discussion (30 min, Video)

• Meet with the Founder

• Discuss working style, ambiguity tolerance, and early-stage expectations

• Questions about company direction and your career goals

Compensation Range: $100K - $130K