Chapter 3

What should your first customer success hire do during the first 3 months?

This is a chapter from The Startup CEO’s Guide to Customer Success and Onboarding.

Common misconceptions:

🚫 Assuming your first customer success already understands and is bought into your company's vision

🚫 Expecting your first hire to hit the ground running on day 1

Starting any job can feel overwhelming. You have new coworkers to meet, systems to learn, and processes to understand. If you're in the market for or just hired that first customer success person, odds are you have a lot of work for them to get started on too.

Having a plan in place for this individual will help you ensure they are empowered to start driving your customers towards unlocking the value of your product or service, and ultimately helping your business retain and grow revenue.

You already know our stance on customer onboarding and we feel the same about onboarding new employees. This is YOUR chance to make a good first impression and set them up for success, both of which directly benefit you and your customers over time.

At a high level, here is what those first 3 months should entail:

Month 1 - Learning

During these first 30 days, the excitement levels are high and new hires are eager to learn. This is your chance to share resources and information to allow them to learn as much as possible.

You can think about categorizing this information into 3 buckets: company, colleagues, & customers.


mission and vision - for the foreseeable future, this first success hire will be the face and voice of your company.

Don't assume your new hire is as bought into your mission and vision as you are; use this time to discuss both. Get their input and answer whatever questions they have on the topic.

This alignment ensures they engage with your customers and future team members with that vision and mission in mind.

  • strategy - shed light on what's worked so far and where you see opportunities to improve. Share any product roadmaps that already exist.
  • access to tools - grant permissions to tools and software they'll be expected to use. Have them explore said tools and software during the first couple of weeks so you can discuss questions.


  • meet the team - facilitate meeting department leaders and existing teams. Invite your new hire to meetings you've already scheduled so you can introduce them. Encourage them to schedule one-to-one time to continue the conversations from there.
  • success evangelist - instill confidence in this person to be the internal champion for all things customer success. Giving them the space to do this consistently will push the rest of your organization to also think from a lens of customer-centricity.


  • recordings and shadowing - share customer call recordings and have them shadow live calls (sales demos and onboarding). The more they learn about your current customers, the better they'll serve your future ones.
  • market and product fit - share thoughts on what you think your current ideal customer profile looks like and the use-cases your customers are coming to you for help solving. Documenting these user personas is a good project for your new hire to tackle in month 1.

Month 2 - Planning

Although learning should never stop, the above should get your success hire ready to do some planning during month 2. Aiming for progress versus perfection is especially important during this stage.

A key component to planning is documenting potential strategies and outlining processes, whether they already exist or need creating.

Do not expect them to solve all of your onboarding or retention challenges right away. Creating an entire customer success strategy takes time and patience. Starting with a customer journey map can prove valuable.

However, this is a great time to double down on that recently gained confidence. Giving this new hire some space to deliver their first "win" will help their confidence exponentially, and ultimately their results.

Here are a few projects that you could consider tasking your new hire with as they apply the knowledge they gained in month 1:

  • design an onboarding framework - onboarding your customers is a critical step in making them successful. Have your new customer success hire plan the steps for onboarding new customers. Setting a goal can help, for example, offer one on one onboarding calls to all new customers within a week of their sign-up date. Our onboarding 101 guide is intended to help with this step!
  • customer success strategy - keeping in mind this is just the starting point, have this person establish a strategic approach to supporting your customers. They won't know all the details right away, however, some specifics to consider are (see chapter 4 for more details):
  • key performance indicators (or KPIs) - retention, churn, and expansion rates (i.e. revenue)
  • targets and goals - number of customers onboarded, renewed, and the touch-points in between.
  • customer engagements - when, who, and how are you contacting customers, building on the "touch-points" in-between from above.
  • expansion and growth plan - when and how are you going to grow these customers
  • design a feedback framework - have this person create a process to capture, review, and share feedback from your customers, good and bad. This way the "voice of the customer" (or VOC) is heard and visible to the rest of your organization.
  • Learning from this feedback is how you'll improve your product and service. Taking action on the feedback shows your customers you value their partnership!
  • more customer calls - continue to join customer calls, but encourage your new hire to lead the conversations. Be there to help answer questions if needed and excuse yourself once you are confident in their abilities. This "passing of the torch" will empower them to take ownership of the customer journey and ingrain further confidence.

Month 3 - Doing

Your new hire has learned and begun orchestrating their plan of attack. Spend some time reviewing the plans and goals, giving feedback and approvals as needed. From there, month 3 is about applying those learnings and executing those plans.

In addition to owning most (if not all) customer interactions, this is a great time for this new hire to:

  • select a customer success platform - you'll need a Customer Relationship Management platform (or CRM) to track customer statuses, notes, and interactions. You'll also need tools to engage with customers, provide product updates, and move them through lifecycle moments (like Arrows for onboarding).
  • Depending on your needs and budget, your new hire should review options and present those that meet your current needs for review.
  • communicate the strategy and goals - as this person documents and creates structure, encourage them to share the progress with your entire organization. This helps solidify their role as "customer success evangelist" and ensures key stakeholders are aware of your customer success strategy.
  • observe and report back - yes, it's still very early, but we assure you there are A LOT of learnings and insights this person will glean from these first 3 months, both about your customers and business. Be sure to dedicate one-to-one time to listen and acknowledge their learnings. Share your thoughts as well to build rapport and trust.

In conclusion…

Regardless of their seniority level, giving your new customer success hire the tools, resources, and confidence to ramp up is critical for their success and the success of your customers.

Be clear with your desires and needs, but also remember that you hired this person to be the expert for all things customer success. Allow them to do that by giving them the autonomy to own, drive, and optimize the process as they go. Neither you nor your customers will regret it.

You can download, edit, and use this template to onboard your new customer success hire!

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