When is the right time to hire your first Customer Success leader?

Congratulations! You're an entrepreneur who's identified a problem to solve and have a vision for how to address it better than anyone else. You've assembled a team and built your alpha product/service, acquired enough users and feedback to shift to beta, and now you can see you're just about to reach the initial summit goal of product market fit. As you're looking at your near-term future, your thoughts are likely shifting from launching the company to preparing it for scale. When you survey your organization do see a hole in your delivery, Customer Success, or overall operations? These tasks are likely being executed by founders or your first round of hires who may not possess the skills needed to take these functions to the next step. You're feeling stuck. You know this is coming and need to answer the essential question when do you pull the trigger and go hire your first true Customer Success leader?

First, you need to do the math. What does your revenue model and sales forecast look like? What is your existing cohort of customers and what's the operating cost to serve them, and future customers? (AKA: you're internal Customer Effort Score)

Next, you need to assess the post-sales team's performance and Customer Success acumen. Is the team rudderless and existing without a defined customer journey and playbooks to guide them? What feedback (if any) do you have from the customer's on their experience post-sales? Do you have aligned upon measurements of success and easy access to reporting and data surrounding it?

Getting solid grounding in the items above will help you understand where both budget and pain reality sit as you will now shift your thinking to the three fundamental paths you have to solving this problem, do you:

1. Build your Customer Success leader inhouse from your pool of existing talent

2. Go to market and hire an experienced Customer Success executive

3. Hire a fractional Customer Success leader from an agency

Each of these paths have different pros and cons for you to weigh, which I've detailed for you below.

Scenario	Pros	Cons	Expectations
"Build" your Customer Success leader from within via internal promotion/hire.	Shows team you're invested in their future, and willing to bet on them like they bet on you. No hiring or product/market education ramp to go through.	Heavy investment to bring someone up to speed. Person will need professional development coaching. You need to accept this person may not work out and you'll end up where you started.	Unless your founders team includes someone with leadership experience at a startup in Customer Success this is the least likely path to generate the outcome you're looking for. Most early stage companies are restricted by their existing talent pool's professional tenure or Customer Success acumen. You're placing a significant bet that this person can handle building a fully functional group with minimal to no experience doing so.
"Rent" your Customer Success leadership from a fractional service provider.	Get the expertise and the execution capabilities without having to carry the additional cost/expense that comes with a full-time hire. May position it with the right provider as a "try before you buy" scenario. (Meaning if you like the provider and provider likes you there's a path to convert from contractor to full-time employee.)	Staff may not fully accept provider proposals or efforts because they're not a member of the company. Team may perceive organization is not "all in" on Customer Success.	Solid "bridge" option as a Customer Success foundation, best practices, and some quick gains will be realized that will position the company well for when business results dictate hiring someone in to the full time role. If you believe you're still more than six months out from needing the full-time hire this is a proven results oriented and cost effective path to take.
"Buy" your Customer Success leader via new hire from outside company.	Strategy and execution owner established. You've declared, and shown, to the company you're serious and ready for Customer Success and you're off and running with it.	You may "jump the gun" and get this hire in too early before you've got enough sales/new customer volume to justify it. You need to assume a six month ramp and initial results timeline.	Best for long term success but really requires business to prove it's ready to scale now, or within six months of the hire date, for investment to make sense.

The decision of when is it time to hire your first true Customer Success leader really comes down to your go-to-market clarity, momentum, and results. Have you moved beyond the perpetual pivot and now possess the sales funnel and wins volume to justify bringing in the expertise to create the strategy, scale, and outcomes to your post-sale operations? If the revenue model shows you're still more than six months out with the need, but your operations for delivering exceptional service to customers is a hot mess that may mean you lean in on the new full-time hire early to ensure the delivery team is stabilized and those customers become evangelists rather than go the fractional route. If you've done the math and think the team just needs an internal "reset" from you then fractional seems the best path. Regardless:

1. Do the math

2. Assess team performance and Customer Success acumen

3. Stay grounded in reality as you may not be ready at all for a Customer Success leader because you still haven't found product market fit!

Leveraging this thinking and the matrix above to help guide you to the best decision for your business for present and future success. If you need further help, feel free to contact me at any time.

Cheers,

Adam