How Any Entrepreneur Can Get Started With Customer Success

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Customer Success is one of the most impactful investments you can make as an entrepreneur. It can provide you with delighted customers who buy more from you, provide testimonials, refer new customers, and renew or expand their contracts year after year.

And the best part? You can start by investing as little as 1 hour per week.

Sometimes known as “after sales service,” Customer Success (CS) centers around optimizing the customer’s experience buying and using your product or service. Other duties may fall under this category, too, such as: onboarding (getting your users set up to be successful with your product or service), training as needed, support if they have an issue, generating referrals so your customers send you more customers, developing case studies that you can use for marketing, and creating best practices to educate customers on how to get the most value out of your product/service.

Step 1: Start with high-value customers first to identify their problems and gather feedback

Start with high-value customers first to identify their problems and gather feedback

If you’re brand new to CS, don’t tackle everything at once. Instead, focus your efforts for maximum impact.

Most early-stage startups get into CS because they’ve been putting all of their time into selling new customers but customers are still leaving (or not renewing). It’s really common when you’re a new business since revenue growth is a matter of staying alive.

Once those existing customers begin to churn (cancel their contracts), the necessity of CS becomes extremely apparent. Instead of waiting for customers to cancel their contracts with you or stop buying from you, I recommend the first CS initiative at your company be to reduce or eliminate customer churn.  

Reduce customer cancellations by getting candid feedback from high-value customers

Start by speaking with each of your customers. In-person is ideal, but over the phone can work too. Start with your highest-value customers, and those closest to their contract end-dates, and work your way down the customer list. Starting with high-value customers is not just about the money but also acts as a signal. If that customer has purchased a lot from you or is continually working with you, they clearly see the value your company provides and will likely have better insight than someone who only purchased from you once.

Give them the TLC that they deserve, get their candid feedback, and evaluate your current position.


  • Thank them for being a valued partner
  • Acknowledge their company’s accomplishments (both related and unrelated to your product/service)
  • Compliment their power users (top performers)

Candid Feedback Questions

  • How has your experience been with our product/service?
  • Have you derived value from our product/service? How much? Any examples?
  • What features/aspects of our product/service do you find most valuable?
  • What would you improve about our product/service? Are there opportunities for us to provide more value?

Evaluation Questions

Talk to your customers
  • Based on the results you’ve achieved so far, do you plan to renew your contract with us?
    • If no: Do you mind explaining why not?
    • If yes: Are there any opportunities for us to provide more value next year? Would XYZ features be valuable to you?

Some questions to ask yourself after all your customer calls (documenting the answers):

  • How many customers currently plan to renew?
  • How many don’t or are unsure?
  • Are there common themes running between your “at-risk” customers?
  • Are there adjustments you can make?
  • What are your top priorities?

Your plan

Always have a plan in reaching out to customers

Come up with a plan to get all of your customers on the path to renew, and don’t be shy about involving your customers in that process! It’s perfectly reasonable to ask an at-risk customer something like “what would it take for you to be confident in your renewal?”

In the beginning, these plans will be reactionary by nature, as you try to course-correct each individual account according to their specific feedback. Eventually, what you should develop are called Customer Success Plans.. These plans help you see very quickly whether a given customer is on track or off track, and whether an intervention is necessary. Having validated customer success plans has been shown to decrease “fire fighting” time by 50%, which frees you and your team to focus proactively on high-value customer initiatives.

Step 2: Upsell and expand through solution brainstorming and interviewing

From the conversations you had with your customers in Step 1, you’ve probably got a good idea of who your top customers or “power users” are. They use your product or service consistently, they recognize the value of it, and they view renewing as a no-brainer. This is the best place to start upsell and expansion efforts.

How do I do upsell customers without becoming a pushy salesperson?

if you alienate customers, follow the tips below to win them back

Instead of seeing yourself as a salesperson, think of yourself as a product expert helping a power-user solve more problems. Ask yourself questions like:

  • Where do you think there are opportunities for the customer to get more value (you can also ask your customers this one)?
  • Why do you see those opportunities as valuable? Again, don’t be afraid to ask customers. If you’re worried about bothering them, send them a casual email asking if they’d mind hopping on a quick call with you to answer a few questions. If they say no, respect that, but many will say yes if you ask.
  • Talk to your customers to hear what they find valuable (Cost savings? Time savings? Better experience?) and then factor those value propositions into your marketing and sales strategies
  • How much more value can you generate? Be sure to frame this in terms of what the customer sees as valuable, since what you think the value of your product/service is may be quite different.
  • Align your product development team (if you have one) on going deeper into the metrics your customers most care about.  

Once you think you have some great recommendations for your customer, feel it out with them. Ask them if your assumptions are correct about the value they could derive if they were to expand their partnership with you. If they say yes, then you’ve established your path to an expansion deal. If they say no, follow up to better understand why your assumptions were incorrect and where more value could be derived.

Behaviours to avoid

In these conversations, do not “pitch” the customer and do not try to convince them of anything. When you’re selling from a CS perspective, you’re a coach on the same team, not a player on the opposing team. Your only goal is to help them solve more problems, so you should only make truly valid suggestions of expansions that are grounded firmly in the idea that the expansions will provide a better return on investment (ROI).

If you push too hard, you’ll lose your customers’ trust and risk alienating them.  

Rebuilding trust

If you’ve already overstepped and worry you’ve alienated a customer or lost their trust, here are a few things to think about:

  • It takes 12 positive experiences to make up for one negative one, so get cracking! Positive experiences could be anything from a handwritten thank you card to a dinner out (depending on budget and location)
  • Having trust means understanding someone else values and believing that they will act in accordance with them. If your company claims to be customer-centric, but you stretched the truth to close a contract, your actions will contradict your values and trust will be lost.
  • Trust has to be earned over time by displaying that your actions do align with the values you espouse.

Step 3: Create a customer experience that encourages renewal and growth

Create a customer experience that encourages renewal and growth

Once your accounts are in a healthy state, meaning they’re renewing and/or expanding their contracts, you can begin to really dig into the customer experience. This is your opportunity to turn users into advocates, generate case studies and referrals to support your Sales and Marketing teams, get customer testimonials, and so much more. It’s time to work on optimizing your customer experience and capitalizing on their results.

Where do I start?

get started with customer success

Begin by understanding your customers’ biggest pain points and thinking about how can you alleviate them. Then consider what opportunities you have to surprise and delight your customers. Bring the customer feedback you receive and the ideas you come up with to your product and engineering teams, if you have them, so that you can work together to prioritize builds based on a balance of customer needs and company goals.

If it’s just you, or you work in services where you don’t have product and engineering teams, speak with anyone that works directly with a customer to talk about ways to delight. This could be something complex like how you deliver your services or something easy like how you answer the phone or greet people in your store or office.

At this point, you can also reach out to your power users to work on case studies, request testimonials, or simply ask “Is there anyone else you know of who you think might benefit from our product/service?” When you take this approach, you’ll be surprised at how many people provide referrals.

For example, when I was in enterprise healthcare software, once I had a great relationship with the head of a given department, I’d ask “Can you think of any other departments that might get a lot of value out of this tool as well?” Nine times out of ten they would say “I think XYZ department would! I’ll introduce you to their department head.” If they said “no,” which some of them did, I thanked them regardless and didn’t push. But because of that strategy and the number of people that were receptive to it, we were able to expand our contracts in such a way that it felt like it was the customer’s idea in the first place, and it gave us credibility every time we spoke with a new department.

The long and winding road of customer success

The long and winding road of customer success

These steps should get you on your way, but they are just the beginning of a long and winding path. Creating success plans, automating CS protocols, optimizing the onboarding experience, figuring out how to measure customer health, and building out your CS team are just a few of the next obstacles for you to tackle.

My advice is to start small, but start early. It’s going to be years before you feel like you don’t need to put out fires all the time, so if your plan is to wait until then to start being proactive, you’re going to regret it. Even if you’re a company of five or fewer people and all you can do is allocate one hour per week to Customer Success, block off that hour, and spend it calling customers, getting their feedback and working to secure contract renewals.

At the end of the day, you’re nothing without your customers, and their success should always be a priority.

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Photos courtesy CS In Focus and Unsplash