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Special thanks to Jonathan Sousa for collaboration in developing this resource. For more information or office hours with Jonathan, see his Operator Network profile here.

Customer acquisition is time consuming and expensive. The best companies take a strategic approach to ensure their customers are receiving maximum value from their products and services. Customer satisfaction, loyalty, and perceived product value directly translates into retaining and expanding revenue.

Enter Customer Success. Customer Success is a critical function that drives product adoption, improves the lifecycle and lifespan with the product, and ensures that usage directly impacts business needs. By establishing this function early-on, you can improve customer loyalty, satisfaction ratings, customer advocacy and references, and drive consistent revenue expansion.

Customer Success vs. Customer Support

Many companies assume they are providing Customer Success when in reality they only offer Customer Support. While subtle, the distinction matters.

Customer Support is reactive and focuses on triaging issues when customers raise them; login issues, billing questions, permissions, etc. Customer Support is operational in nature, focusing on core speed and quality metrics to deliver a timely response to customer questions. The function is rarely accountable for revenue goals.

Customer Success is proactive and focuses on revenue retention and expansion through strategic customer management. Customer Success usually includes onboarding, training, and influencing adoption and value from the product. Customer Success teams serve as the bridge between customers and internal teams, providing feedback and insights, while building customer relationships and positive customer heath scores.

Customer Success Goals

While most large companies have a formal Customer Success team, smaller startups can benefit from a structured Customer Success (CS) function. Early-on the function can be led and managed by the founder; high-touch and highly focused on success outcomes. As the team grows, the founder can step away from these duties, but the focus on engagement and outcomes should remain.

Regardless of stage or size of company, CS should contribute to 4 main goals:
  1. Improving Renewal Rates- by ensuring customers are achieving their business goals and receiving value from the product.
  2. Expanding Revenue- by upselling and cross-selling other parts of the product.
  3. Limiting Churn- by ensuring alignment with customer expectations, and identifying critical feature and functionality gaps to inform your product roadmap.
  4. Developing Customer Loyalty- resulting in references and case studies that can be used in future sales motions.

CS Lifecycle

Customer Success should own the customers’ post-sale journey, with responsibilities grouped into four components. Onboarding, implementation, adoption, and retention. Here is a helpful checklist to help you navigate the process and details about each step can be found below.


Setting expectations and outlining how the customer will receive value.

Onboarding is a fundamental step to confirm what you learned in the sales handoff and ensure alignment around customer expectations. It’s an opportunity to clearly define timelines, potential roadblocks, and quick wins for early customer adoption.

First impressions are everything - these first post-sale interactions are critical in setting the stage for how your team and the client will work together over time. Purposeful response times, clear documentation, and quick implementation cycles will get you started on the right foot.


Identify what milestones must be achieved for the customer to feel their implementation was a success and that they’ve found value in their purchase. Create a joint roadmap outlining how your team will support them in achieving these goals.

Key Steps:

Internal Handoff

Target Timeline: Immediately after customer purchase

Right after purchase, it’s important to immediately communicate next steps and points of contact. Whether your CS is founder-led or you have a Customer Success Manager (CSM), jump-start the onboarding process by scheduling a kickoff meeting with internal team members to make sure that you have a consistent understand of the customer’s goals and expectations.  

Onboarding Kickoff Meeting

Target Timeline: Within 14 days of customer start date

This is an hour-long meeting where you should confirm the business goals and customers expectations, while ensuring you’re aligned with the customer on what comes next. It could include any technical team members responsible for setting the customer up, and the sales team member who handled the pre-sale conversations to ensure continuity. The goal of the meeting is to establish a collaborative relationship that leads to the customer finding value in the product.

Key Things to Understand and Reiterate from the Pre-Sales Process:

  • Why did the customer choose to purchase your product at this moment in time?
  • What core challenge are they trying to solve?
  • What other products or services are they using?
  • What are their business goals? Both short and long-term?
  • Who’s responsible on the customer’s side to ensure the product will get implemented?
  • What other stakeholders are involved in this process?

Clearly communicate implementation logistics and timeframes, including when the customer can expect to be fully integrated, training or support that’s included, and if applicable, what you’ve seen work with other customers and how that can translate to their implementation experience. Be sure to clearly articulate what you expect from the customer, too, for them to achieve the results that they’re looking for.

Once you align on the implementation plan, establish a regular check-in cadence as they continue onboarding onto the product or service. (Note: customers will get frustrated if they have to repeat themselves about their goals and what’s needed for their implementation. Establishing how often you will communicate and taking thorough notes is a major component of setting expectations and achieving customer satisfaction.)

Here’s an example of a kickoff deck to use as you design your onboarding journey.

Share Your Customer Success Plan

Target Timeline: 1-2 days after the kickoff meeting

After reviewing the desired outcomes discussed during the kickoff meeting, use those goals to outline the milestones and timeframes needed for successful adoption of your product. Follow up with the customer by sharing a document that summarizes this information and includes an implementation plan.


Getting the customer up and running with the product.

Depending on your product, implementation can take a few minutes or six months+. CS’s role is to oversee implementation and to provide user training and guidance as the customer begins to use the product. This is a critical stage in the journey, as missed timelines or confusing user experiences can result in poor customer engagement and lead to a perceived lack in product value.


The goal is not to simply provide access to the product. Proper implementation ensures usage and showcases the products value. An effective implementation should aim to get the product up and running and the client informed/ trained in how to use functionality for their use case.

Key Steps:

Training Workshop(s)

Target Timeline: While implementation is being completed and/or after successful implementation

Provide customers with a tutorial or walkthrough - what to expect, how to use the product, and how they can leverage functionality for their unique use case. If you have a straightforward product, it may be as simple as sending a getting started email or video. More complicated products may require multiple live training sessions.


Helping customers use and get value out of the product.

As opposed to the finite onboarding and implementation processes, adoption is the ongoing task of getting purchasers to use the product over time, so that they can see and benefit from the received product value.

Customers should fully understand how the product works and be informed about new or upcoming functionality. CSMs should regularly assess if their clients are leveraging all functionality relevant to their use case and business goals. Every company will have a different lens they take to assess usage - for a data company it might be identifying how frequently a reporting dashboard is viewed, for a product-led growth company it might be tracking how many of the purchased licenses are utilized.


Adoption is about identifying the critical features needed for the customer to achieve value and helping customers navigate and enjoy those functions independently.

Key Steps:

Quarterly Check-in

Target Time: First check-in should be in the same quarter as the customer’s contract start date

Review how deeply the customer has leveraged relevant features/functionality and if they are on track to achieving their business outcomes in relation to your product.

Quarterly check-ins should be ~30-45 minutes. Before the meeting, share an agenda and ask the customer to contribute to the plan with any relevant questions or topics they would like to discuss. This will allow the customer to come into the meeting with the right expectations.

Example Agenda:

  • Recap the implementation process
  • Share usage metrics (ideally, include metrics that emphasize usage is taking place and value is being received)
  • Review of what’s upcoming - product updates, meetings, events, etc. that might be relevant for the customer
  • Open questions from the customer? Feedback from the customer? Anything else the customer needs?

Retention, Renewal, Expansion

Growing customer spend within and across products.

The ultimate metrics for Customer Success should be revenue retention and expansion. Are customers continuing their relationship with you, are they renewing their contracts at the same or increased level as the year before, and are they requesting to expand their usage into different product verticals or feature sets?

While renewals timelines are dependent on your contract terms, companies should start preparing for renewal conversations 6 months ahead of a contract end date. This will allow enough time to assess and influence product usage, create excitement about the future product roadmap, work to build supporting relationships within their customers’ users, and right the ship if there are any roadblocks or issues.


Ideally, renewal conversations are a non-event because the Customer Success team has shown value and positioned the renewal as a continuation of a strong partnership. The conversation should be less about renewal and more about how expanding usage and how this might benefit their future business needs, centered around the idea of continuing a valuable partnership vs. a dollars-and-cents negotiation.

Key Steps:

Mid-Point Check In

Target Timeline: 6 months before contract end date

The team should pull metrics on overall usage, unused licenses, key feature usage, and relevant user feedback during this meeting. The goals is to review the customer’s progress to date, gauge customer happiness, and seed the idea that a renewal is coming up.

Renewal Notice

Target Timeline: 90 days prior to renewal

Notify the customer of the renewal date and surface relevant product updates that might be of interest, but also take this time with the customer demonstrate how you’re providing value to the customer. This meeting should take ~30-60 minutes, depending on the size of your company.

Renewal and/or Upsell Proposal

Target Timeline: Maximum a month after your renewal conversation

Showcase how new features or expanded usage could help the customer in additional use cases. There should be 2-3 options for the customer to decide between, with proposals that have mutual benefit for the company and the customer (ie. better pricing for longer term, incentives to build footprint, opportunities to lock in a public reference).

Preparing and Sending the Renewal Contract to Customer

Target Timeline: 15-30 days prior to renewal

Prepare a new contract for your customer and execute the agreement with their team.

CS Strategy

Identify Your Ideal State

While Customer Success is a post-sale function, your vision for what CS should be for your business should be mapped out well before a customer walks through the door, and the ethos for making customers successful should be shared across the company. A strong CS process is forward-thinking and focused on achieving the ideal customer journey - what do you want the customer experience to be and what does ideal usage look like over time.

Whether it’s an engineer integrating the product or the CEO handling the kickoff conversation, your ideal state plan should include an overview of the typical customer journey, key stakeholders, critical action items at each stage in the customer lifecycle, and an internal owner who is responsible for every step.

Create MVP Documentation and Training Materials

While creating some training materials and product documentation is helpful, the reality is that many customers do not read through these documents. They are also prone to becoming outdated when there are frequent product changes and updates.

We recommend building a MVP set of documents that can help a customer get up and running and/ or address common questions and focusing more time developing your onboarding and implementation processes.

The caveat is for Seed or very early-product companies who are working with design partners. These early customers are taking a gamble on your product and will require white-glove service so they can provide detailed feedback and product insights.

Build Your Risk Framework

Every customer relationship has some level of risk. Even the most established companies can lose budget year to year or change direction, leaving your product on the shelf. Identifying these potential risks early and often is the key to effectively managing customer relationships.

We recommend all companies create a customer risk framework and identify potential pitfalls with each customer relationship. This framework can then be used to develop a set of action steps to effectively respond and/ or mitigate issues.

Note: Not all issues are fixable. It’s important to try to resolve customer issues whenever possible, but it’s also important not to change your companies direction based on a single customer. If there is a fundamental difference in goals or the ability to address a customer’s needs, it’s OK and recommended to move on. Don’t spend unnecessary time trying to solve for a problem that cannot be fixed.

Metrics & Reporting

Quantitative Metrics

There are two quantitative factors all companies, regardless of stage, should regularly measure:

  • Time to implement: The time it takes to integrate your product into the customer’s workflow.
  • Time to value: The point in which the customer sees value from the product.

Incorporating these factors into your metrics will look differently depending on your company and customer. For a user-driven video platform, it could be centered on time to value - how many videos are people recording or sharing across teams? For a technical data product, it could be around licenses used - are customers leveraging 90% of the licenses they purchased?

In addition to time to implement and value, companies with a growing customer base should also start to track some additional metrics to ensure their customer success efforts will result in renewals and increased profitability.

  • Net Dollar Retention (NDR): Calculates how much your revenue has grown or shrunk, including any revenue retained through upsells or cross-sells.
  • Gross Retention Rate (GRR): Measures recurring revenue retained, but doesn’t include expansion revenue.
  • Customer Health Score: Includes various inputs on how customers are using or adopting the product,  indicating if that customer will grow, renew, or churn. You should build a score that incorporates both quantitative metrics and qualitative metrics, to get a balanced view of how customers are feeling and performing.
  • Money Under Management: Refers to the total amount of money managed for all accounts or for a specific customer.
  • Number of Accounts: Indicates how many active accounts the company has.

For additional information about customer success metrics, HubSpot has a great article diving into each.

Qualitative Metrics

While slightly harder to measure, qualitative metrics are equally important and should center around how you’re delivering on a customer’s key outcomes.

There are two main ways to gather this information:


Rather than NPS, run surveys that gauge how your team and product are meeting customer expectations.

You can ask questions like:

  • “0 to 10: to what degree are we meeting your expectations?”
  • “What would make us 1 rating higher?”

Early on, it doesn’t have to be a formal survey and you can tailor questions to the customer. As you grow the survey should become more standardized and be sent out at the same intervals in each customer journey.

Customer Conversations

While surveys are a helpful tool in gathering feedback, they are not a replacement for regular, live customer conversations. Check in with your customers regularly and empower them to give feedback on their experiences and usage.

Live conversations are a powerful way for customers to articulate what’s working and not working across the product, feature sets, or even implementation. For highly engaged customers or design partners, best-in-class teams will ask users to perform a demo using the product in real time.

Hiring & Compensation

Early-on founders will typically function as the Customer Success Manager (CSM). However, as the company and customer-base grows there will come a point where the founder is stretched too thin and will not have the bandwidth to give customers the hands-on service they expect. At this stage, it’s time to hire your first CSM.

Identifying the Right CSM Profile

There are two CSM profiles to consider when hiring your first candidate:

  • Technical: Technically-inclined, can find their way around the product and deploy more complex configurations for customers.  
  • Relationship-driven: More relationship-oriented and will drive renewal and expansion conversations.

Depending on the skills and experience needed, pick one type as your first hire then the other as your second. If your product is quite technical and the CSM will need to configure customer workflows and perform extensive implementations, choose a more technically-inclined candidate first. If the product is relatively straightforward to implement and less sticky (low barrier to switching), a more relationship-driven candidate may be needed.

Many companies tend to under-hire and opt for a very junior/ inexperienced candidate to start. While a Director+ level candidate is not needed, a strong first hire should be experienced with customers, strategic, and able to clearly define processes that scale. This person will likely be responsible for growing the team and developing the CS team structure. Because of this, we recommend hiring a more experienced CSM to start.

Assessing CS Candidates

Assign a project as part of your hiring process. A mock quarterly business review (QBR) is an exercise that can work well to demonstrate a candidate’s strategic mindset. In the real world, this is a regular meeting with your customer to discuss how you can continue to support them. For a project, you can create a sample prompt that outlines a sample customer situation with mock data and have the candidate walk you through how they would approach the review.

Structuring a Mock QBR Interview

  • 10 minutes discussing the strategy of how the candidate approached the prompt.
  • 30 minutes having the candidate present the report.
  • 20 minutes discussing feedback and Q&A.

What to Look for During the Interview

Presentation Skills
  • Is the deck presentable? Do they have a high bar for quality that would represent your company well?
  • Does the deck have clear and understandable flow?
  • Is the candidate setting the stage and managing the conversation toward a set of goals?
Industry Knowledge
  • Are they covering obstacles and challenges for the customer?  
  • Are they highlighting the utilized features and orienting around value for the customer?
  • Did they spend time on notable wins?
Strategic Thinking
  • Are they showing data that ladders up to customer's target metrics?
  • Are they giving an opportunity for feedback and opening the conversation for potential renewal or additional products?  
  • Are they positioning the data to deliver an outcome that benefits both the customer and your company?

CS Teams as You Scale

As you grow, your CS team will include relationship managers, account owners who drive commercial outcomes, technical implementation, and dedicated support functions (usually its own function under Customer Support).

Once your CSM jobs have been defined, we recommend keeping your CS career levels simple. After 2-3 general CS levels, develop two separate career tracks (individual contributor and manager) and define the skills needed for each position for transparency and employee satisfaction.

IC Track

CSM 1 - Customer Success Associate

Entry-level, assists CSMs with their accounts or work with smaller customers due to limited experience and knowledge of the product.

CSM 2 - Customer Success Manager

Manages own accounts with little oversight.

CSM 3 - Senior Customer Success Manager

Manages more complex clients.

CSM 4 - Customer Success Director

Manages a few large accounts (i.e. Amazon, Microsoft) that involve heavy complexity and relationship-managing (proper management of each account should take 10-15 hours per week).

CSM 5 - Senior Customer Success Director

Manages most complex clients and serves as a thought leader for company and industry.

Management Track

MGR 1 - Manager, Customer Success

Manages a small number of junior CSMs, may start as a hybrid IC role and transitions to a full-time managerial role over time.

MGR 2 - Senior Manager, Customer Success

Manages a full team of CSMs.

MGR 3 - Director, Customer Success

Manages multiple CSM teams.

Incentives and Compensation

In the early stages, it’s best to keep compensation and incentives straightforward: only base + equity to start.  

As your company grows and gets repeatability in the business, it may be worth adding variable compensation (only if there are metrics that the CSM has direct ability to influence). Variable pay could be based on an expansion targets or on renewal percentage, but shouldn’t be based on adoption targets unless the CSM can truly drive adoption metrics - this will vary by product. For additional information about variable compensation, check out our Sales Process guide here.

Tools & Systems

Included below are a list of tools, documents, and systems to help streamline customer success processes as you scale.


For founder-led CS functions, we recommend using a spreadsheet to keep track of customer notes and feedback. Keep it simple, include your contracts, what did they buy, when do they renew, etc.

Early Team

Early CS teams should unify their notes and data using a tool like Vitally or Catalyst (see options below).

Scaled Team

As your team grows, you operationalize your customer success function through automating, parts of your onboarding, surveys and feedback collection, and customer marketing and messaging using some of tools mentioned below.


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