Hiring Your First Digital Customer Success / Tech Touch Rep: What to Look For and What to Avoid

If you’re building a Digital Customer Success (DCS) or Tech Touch motion from the ground up, one of the most important hires you’ll make is your first dedicated rep. This isn’t your average CSM role. It’s part customer success, part operations, part sales, and part….. marketing? More on that later. You’re not just hiring someone to manage accounts, you’re hiring someone to help scale a strategy.

I’ve built these teams myself, and if there’s one truth, it’s this:

Hiring the wrong person will slow everything down. Hiring the right person can 10x your impact.

Here’s how to think about hiring your founding Digital CS/Tech Touch rep, what traits to look for, and what to avoid at all costs.

First, Understand What the Role Really Is

This person won’t be booking quarterly business reviews or running calls all day. Instead, they’ll be:

• Managing hundreds of accounts and users with automated engagement

• Running 1-to-many onboarding, adoption, and renewal campaigns

• Working inside your CRM, automation platforms, and email tools

• Triaging accounts that need human follow-up vs. those that don’t

• Building out playbooks and feedback loops from customer behavior data

This isn’t about volume-based customer support. This is about scaling strategic post-sales without throwing people at the problem.

What Makes a Great First Digital CS/Tech Touch Rep?

✅ Process-Oriented Thinkers

They thrive in systems. They like workflows, documentation, and understanding how all the puzzle pieces fit together. They’ll spot inefficiencies fast and aren’t afraid to build or refine processes from scratch.

✅ Comfortable with Tech (Not Just Using It — Owning It)

They actually use tools, not just log in. Whether it’s creating email sequences in HubSpot, running a report in Salesforce, or setting triggers in Intercom, they’re comfortable working under the hood. Tip: If you’re unsure who this is, ask your vendors who some of your top power users are in your organization.

✅ Strong Written Communicators

Remember, odds are, this person isn’t going to be on Zoom with customers often. You're hiring for clear, concise, scalable communication. Most customer engagement will happen via email or in-app, so they had better know how to write for impact. While marketing might provide content that highlights the value of your solution, your ideal candidate knows how to adapt that messaging to feel more human and relevant. They can take polished marketing copy and turn it into something that speaks directly to a customer’s pain points, bridging the gap.

✅ High Curiosity, Low Ego

They ask “why?” a lot. They’re not afraid to challenge broken processes. And they don’t need constant hand-holding. This role will evolve as the program scales, they need to be flexible, self-starting, and hungry to learn.

✅ Light Ops or Automation Background (Big Plus)

Bonus points if they’ve played in CSPs like ChurnZero, Gainsight. However, the can be familiar with sales engagement platforms, like SalesLoft or Apollo.io, or even Marketing automation platforms like HubSpot. Even better if they’ve run automated campaigns or know what a renewal workflow looks like behind the scenes.

✅ Data-Driven and Outcome-Oriented

When you’re launching automated emails or workflows, you need data. A strong Tech Touch rep is comfortable with basic data like click-through rates, engagement drop-off, health scores, customer personas, etcetera. They use data to prioritize, optimize, and segment their customers. Bonus points if they’re comfortable with dashboards, report building, or using analytics tools.

What to Avoid (Even If They Look Great on Paper)

❌ Traditional High-Touch CSMs Who Can’t Scale

If they’re used to holding the client’s hand at every step, this won’t be a good fit. This role is about efficiency. You need someone who can say, “How can we do this once for 500 people?” not someone who thrives on 1-to-1 relationships.

❌ Disorganized or Reactive Operators

This person will own hundreds, maybe thousands, of accounts. If they can’t stay organized, keep clean notes, or track what’s been sent to whom, things fall apart quickly. You’re not looking for someone who “wings it.” You need someone who thrives in process, keeps systems up to date, and can run an efficient program without dropping the ball. Disorganized = disaster in this role.

❌ Too Junior, Too Green

This hire will need to operate independently and make judgment calls. You don’t need a VP, but you do need someone who can figure things out without a detailed playbook every time.

❌ Over-engineers Who Overcomplicate

Yes, some people love building, but you don’t need a 75-step Zapier flow and six dashboards for a simple onboarding nudge. Look for someone who keeps it simple, executes fast, and iterates later.

Interview Questions to Surface the Right Candidate

• “Walk me through a process you’ve helped automate.” Look for understanding of goals, tools used, and what changed after implementation.

• “If you had to onboard 200 accounts in 3 months, how would you approach it?” You want to hear about segmentation, email journeys, self-service content, and tracking.

• “What tech tools are you most comfortable with?” Not just what they’ve used, but how they used them and how deep they went.

• “Tell me about a time you managed a project without much guidance.” You’re hiring someone to own a segment. If they need a babysitter, it’s a hard pass.

Final Tips

• Start with a contractor or pilot role if you’re not ready for a full-time hire. Just make sure they’re scoped to build, not just “check in” with accounts.

• Define what success looks like upfront. Time-to-onboard, engagement rates, renewal lift, whatever matters, write it down.

• Have them run a sample automation or email journey as part of the interview. If they can’t think through a simple renewal campaign, they’re not ready.

TL;DR: Your First Tech Touch Rep is a Multiplier

If you’re investing in Digital Customer Success or Tech Touch, your first hire will make or break the program. They’ll own the early processes, test automations, and set the foundation for scale. So don’t just look for someone with “Customer Success” in their title. Look for a builder. A thinker. A doer.

Get that right, and the program practically runs itself.