The opportunities for Customer Success

Rav Dhaliwal
6 min readJul 15, 2024

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A version of this article first appeared on the Scottish Equity Partners website

The drive for efficiency

As start-up boards continue to look for greater efficiencies, Customer Success (CS) teams have borne the brunt of company restructuring and layoffs over the last 18 months.

Headcount and budget reductions, prolonged hiring freezes and letting go of (sometimes high profile) Customer Success leaders has become increasingly common, as have discussions on utilising AI to engage customers as a means to reduce monthly “burn” and extend financial runway.

The hidden opportunity

Whilst ongoing constraints in both the macro-economic and tech funding environments continue to present existential challenges for Customer Success teams, it also affords them a unique opportunity.

Specifically, the opportunity to alter the ingrained perception held by many start-up boards and investors that Customer Success is not an integral part of the start-up’s revenue generation engine and is therefore a less risky part of the business to target for any round of cost-cutting.

With this in mind, the following practical steps, which importantly are completely within the control of both individual Customer Success practitioners and their leaders, should prove valuable in helping to alter this long held perception.

The practical steps

Step 1: Speak the (internal) language of revenue

By the nature of their work, Customer Success teams are outwardly focused, meaning their activities, language and general frame of reference are predominantly external to the business that they work in.

This makes sense, but it can lead to the perception internally that Customer Success is only focused on helping customers to achieve their goals and is not fully aligned or contributing to the start-up’s own revenue objectives.

Treating their board, investors and senior leadership team as their “internal customer” and communicating with them in a language they are familiar with — the language of revenue, is a simple and effective way for Customer Success practitioners and leaders to better demonstrate their alignment to revenue goals. For example -

CS language vs Revenue language

  • “I have 20 customers” -> “My territory is $3.1M ARR in size”
  • “Customer X upgraded to module Y” -> “We grew revenue from Customer X by 12%”
  • “We have 2 new case studies” -> “We contributed to top of funnel growth by closing 2 new references”
  • “We have 8 customers in onboarding” -> “We are forecasting 8 new customers live by quarter end”

Step 2: Territory planning, reporting and forecasting

Boards, investors and senior leadership teams often perceive Customer Success in the same way as they do Customer Support — as an inherently reactive and transactional function that is not directly linked to revenue.

Territory planning, reporting and forecasting are practical ways individual Customer Success practitioners and leaders can operate and communicate differently to combat this misconception. Specifically -

  • Organising, tracking and reporting on their “assigned territory” as opposed to their “assigned customers” given the formers stronger association internally with revenue
  • Setting, tracking and reporting on the progress of quarterly targets for their territory, including month-on-month and quarter-on-quarter comparisons.

Examples of quarterly targets to track in a CS territory plan that would resonate with the board and investors include (but are not limited to) -

  • Licence activation growth
  • Product and/or key feature adoption
  • Consumption growth
  • Deployment / onboarding completion
  • Gross Revenue Retention*
  • Net Revenue Retention*
  • Referenceable customers

* Regardless of whether Customer Success is officially measured or compensated on revenue, setting, tracking and reporting on revenue targets for a given territory is a subtle yet visible way for CS to associate its work with metrics that are materially important to the start-up’s leadership.

  • Forecasting is the critical process by which businesses make decisions. By developing a quarterly forecasting and reporting “muscle” for their territory targets (especially in relation to gross and net revenue retention*), Customer Success can actively demonstrate its proactivity whilst further strengthening the association of its work to the start-up’s revenue generation engine.

Step 3: Get connected to the sales pipeline

With its place at the tail end of the go-to-market production line, Customer Success is often partially or completely disconnected from the sales process, with little or no understanding of the critical contextual information it needs to drive fast time to value, for example -

  • What pain the customer is looking to solve
  • The impact of the pain and how they are dealing with it now
  • The objections they raised in the sales process
  • The competitive alternatives they considered
  • The stakeholders involved in the purchasing decision
  • Their buying / procurement process

This disconnection can reinforce board and investor perceptions about Customer Success not being integral to revenue, however the following actions can help to minimise this view and most importantly do not require any formal approval or mandate -

  • Reviewing the Sales forecast regularly, both individually and as a team, and using it as a key input for CS territory planning, targets and forecasting
  • Informally assigning / attaching team members to key deals to uncover critical contextual information via informal 1:1 discussion with sellers
  • For CS leaders in particular, organising to be an observer at Sales forecast calls and offering to help accelerate deals if appropriate with customer use case examples or customer introductions

These actions foster closer alignment to revenue and over time, hopefully crystallise into Account Executives, Sales Engineers and Customer Success Managers working more closely together for mutual benefit in formalised “pods”.

Step 4: Refine and develop common Sales skills

Commercial aversion in Customer Success often results from having been at the receiving end of poor sales practices.

Regular exposure to a company’s best sellers however would (no doubt somewhat surprisingly to many in CS) reveal a great deal of commonality in both activities and skills. Specifically -

  • Problem and pain discovery
  • Identifying success criteria
  • Building ROI cases
  • Project management (e.g. of deals)
  • Handling objections
  • Influence and negotiation

Seeking out their company’s best sellers and asking to shadow them at different deals stages (or listening to recordings of their sales calls if available), would not only help Customer Success practitioners to sharpen and refine these skills, it would also expose them to valuable additional ones such as -

  • Opportunity identification, logging and qualification
  • Gaining access to & managing multiple stakeholders
  • Effective cold outreach
  • Gives & gets
  • Driving urgency

Developing these additional skills, especially in opportunity identification and logging, should help Customer Success to gain much greater internal recognition as a meaningful contributor of high-quality opportunities to the sales pipeline whilst also increasing familiarity with the internal language of revenue.

In addition to informal shadowing and learning, Customer Success leaders should also consider having their teams “piggyback” on any existing or planned Sales training, especially in the aforementioned common skills areas.

Combining the training of Sales and CS teams this way should provide greater economies of scale (especially in times of constrained budgets) and can be further justified by the increase in qualified opportunities that should result.

Step 5: Ring the “Sales bell”

Good sales leaders continuously shine a light on the impact their team is having on company goals through regular internal communication across multiple different channels.

Whether it is through sales dashboards, charts, presentations at company town halls, board meetings, quarterly kick-offs, or utilising the myriad of company-wide internal communication tools, good Sales leaders habitually share the outcome of their team’s work.

This regular cadence of communication serves to continually reinforce how their work is directly aligned to the company’s goals and objectives and is best exemplified by “ringing the sales bell” — a company-wide post or message that Sales leaders share every time a new deal is closed.

There is nothing preventing Customer Success leaders from mirroring their Sales counterparts with regular communication across internal channels when CS territory goals are met or exceeded, in particular -

  • GRR and NRR*
  • Renewals closed**
  • Upsells closed**
  • Churns that are prevented
  • New references closed
  • Consumption goals

** Even if Customer Success is not responsible for transacting renewals or upsells, sharing these positive results (along with credit to any other roles involved), reinforces how their ongoing work with customers has created the conditions for these renewals and upsells to occur.

Additionally, Customer Success leaders should collate their quarterly territory data (including quarter on quarter comparisons) into 2 or 3 succinct slides with an explanatory narrative to be included in the board pack, and if needed they should push to present these slides in person and take questions at the board meeting.

Summary

A common refrain amongst Customer Success leaders is that unlike their sales counterparts they “do not have a seat at the table”.

By embracing the language of revenue, operating in terms of territories, proactively connecting to the sales pipeline, refining common sales skills and developing valuable new ones, wrapped up in a regular cadence of internal communication, Customer Success can not only begin to alter some of the long-held perceptions that put it at risk, it can also strengthen its case for representation at the all-important decision making table.

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Rav Dhaliwal

Investor, Board Member, Venture & Limited Partner @crane_vc . Alumni @slackhq @zendesk @yammer @salesforce and others.