The Blueprint for Subscription Success in 2020

If you’re responsible for revenue at a SaaS, online subscription, or membership organization, this is for you. With 15+ years of experience in the online subscription space, I’ve built a tried and true framework for achieving organizational health for online recurring revenue businesses.

If the following 5,000 or so words resonate with you, there’s a link at the bottom to request a free 60-minute strategy call with me.

Treat this article as a litmus test: how does your business stack up to what a healthy, thriving, wildly profitable subscription company looks like?

It might seem obvious to start by picking on Sales.

After all, sales takes a lot of heat when things aren’t looking so good. They are often the squeaky wheel in an organization, and my job is to help provide the grease.

But I often find that Marketing, Customer Success, and Product all need a little grease too, to make the subscription flywheel spin in perpetual motion. Product is the linchpin of the flywheel. But that flywheel won’t turn a single revolution without tight collaboration with the revenue generating arms of the business: Marketing, Sales, and Customer Success.

The degree to which Product successfully communicates with Marketing, Sales, and Customer Success (as they are all inextricably connected) directly affects sales & expansion revenue – and therefore organizational health.

A SaaS, subscription, or membership company that can communicate well internally and work toward a common goal can scale faster, more effectively, and more profitably than one with siloed departments with ever-increasing levels of resentment for one another. That’s obvious, right? Not so fast.

Take quick stock of the degree to which your Leadership would agree with the following:

  • Everyone in the organization understands the vision/goal(s) of the business and are rowing in the same direction
  • Standard operating procedures (SOPs) are documented, implemented, and refined in every area of the business
  • Cross-departmental communication is strong & departments are strategically aligned
  • An intentional company culture is being cultivated & employees demonstrate a strong cultural fit
  • Customer Success thrives at onboarding, retention, aiding in expansion revenue, engagement tracking, community curation, customer service, and off-boarding

Would each member of your Leadership team provide the same answers to these questions?

  • Where is the company now? Where do they want to be? What’s keeping them from getting there? (Current state vs. future state + known blockers)
  • Why is the company in business? (What’s the True North?)
  • What is the organizational decision making hierarchy and process?
  • How does the organization respond to failure?
  • How is the company’s culture defined and embedded into the fabric of the organization?
  • What are the most glaring surface level organizational problems? Deeply ingrained systemic problems?
  • What are the organizational KPIs and who is responsible for each?
  • What are the company’s core competencies?
  • How are expectations set and met (exceeded!) throughout the customer journey?
  • How is product pricing being tested on an ongoing basis?
  • How is expansion revenue being monitored and maximized?
  • How is individual and departmental accountability tracked and measured?

Throughout any engagement with a subscription based business, I take a holistic approach to organizational health. Leadership, strategy, operations, finances, and people are the lens through which I see the following 4 core areas of focus in a subscription business:

  1. Marketing
  2. Sales
  3. Customer Success
  4. Product


*My primary goal for SMB (small & midsized businesses): build a robust email list of qualified prospects from which to strategically nurture (via email, re-targeting campaigns, influencer relationships, content) based on each prospect’s stage of awareness. Then, successfully hand off sales-qualified leads (SQLs) to Sales at the appropriate time.

  • Your subscription can’t appeal to and please everyone – narrow the playing field by pinpointing exactly who your most ideal customers are. Start by creating ICPs (ideal customer profiles)/customer personas based on current subscribers who could be classified as Power Users. Power Users have the highest cLTV (customer lifetime value) and are the most loyal product evangelists. What was their buying journey? What objections did they present? Which outsiders influenced their purchase decisions?
  • Create an Influencer Map based on who influences the purchase decisions of each segment of the company’s target prospects. This can be as simple as coming up with a list of bloggers, podcasters, industry celebrities, social media accounts, etc. that your ICPs are engaged with and trust.
    • What relationship exists between each influencer and the company?
    • What does a fully leveraged influencer partnership look like and what will it take to get there with each influencer?
  • It’s key to properly segment prospects and create Influencer Maps and marketing campaigns for each ICP. Segmentation and hyper-personalization for each ICP will amplify your marketing efforts, increase the percentage of qualified inbound leads, shorten the sales cycle, and increase retention. A prospect who fits one of your ICPs should see your marketing and say, “Wow, they really get me!”.
  • Identify marketing channels chock-full of power user lookalikes and strategically use influencer partnerships, content marketing, and social media, to amplify reach and credibility with ICP segments.
  • Create a hyper-personalized campaign that includes multi-channel touch points, delivered at an appropriate cadence, for each ICP.
  • Relentlessly plan, deploy, and assess tests to determine the most viable lead generation channels for the company: set campaign goals, campaign parameters (budget, timeline, platform, etc.), decide how results will be assessed, and run it. Rinse and repeat.
  • Key elements to a successful lead generation campaign:
    • Present a compelling offer & corresponding CTA(call to action) to prospects in exchange for their email address. This offer is called a lead magnet and can come in the form of a white paper, list, webinar, quiz, assessment, and more.
    • The offer should serve as a pain killer by solving an immediate/urgent problem for the prospect as well as speak to how your solution will fulfill their foundational desires, e.g. peace of mind, success, recognition, etc.
    • The lead magnet offer must be directly relevant to the company’s core offering and match the prospect’s stage of awareness (more on stages of awarenesses in the next section).
    • Start setting appropriate expectations from the first marketing touch: what outcomes can your customers truly achieve through your offering? My philosophy is underpromise, overdeliver + delight = Power Users
    • Include testimonials from Power Users and/or other social proof.
  • Create SOPs for top of funnel (email list building) efforts for ease of implementation, consistency, and transferability to other staff.
  • Utilize an appropriate tech stack for planning, implementation, and assessment of marketing campaigns, ideally one that integrates with Sales’ CRM.
  • KPIs (Key Performance Indicators) for Marketing: CAC (customer acquisition cost), CAC:LTV ratio (how much did it cost the company to acquire a new subscriber as compared to the amount they spent with the company over their tenure as a subscriber), conversion rates & timelines for every stage of the marketing funnel. Proper attribution of leads is also necessary for improving decision making for future marketing campaigns.
  • Marketing must clearly and consistently communicate with:
    • Sales to determine the parameters and definition of a sales qualified lead as well as how & when to hand-off prospects to SDRs (sales development reps) or sales reps.
    • Product to have an in depth understand of the product, feature roadmap, etc.
    • Customer Success to best understand the customer journey of Power Users so they can reverse engineer their efforts to attract more of those subscribers and set them on that same path.


At its core, I believe that sales is problem solving. B2B sales teams must be able to effectively diagnose and frame business problems to a buying committee, and then present creative solutions to solve that problem. They must be able to quickly and effectively become fluent in prospects’ industries; tease out problems, objections, and key stakeholders; then design a solution to bridge those gaps and present it at the right time, to the right people.

The most successful salespeople do what they say they’re going to do when they say they’re going to do it. They are relentless in their pursuit of excellence and exceeding customers’ expectations.

For Sales to be successful, fluid communication with Marketing, Customer Success, and Product is absolutely necessary, as is proper technology (CRM software, etc.), implementation, and adoption amongst sales staff.

Comprehensive discovery is key to a successful selling relationship. Seek first to understand, then, and only then, to be understood. Incisive and thoughtful questioning is the foundation from which to build the case of how your solution can deliver the outcomes your future subscriber needs and expects.

As the old adage goes, nothing happens until someone sells something. Let’s dive in on how to sell subscriptions.

The following represents the broad strokes of what a healthy sales department looks like at a subscription-based organization. This serves as an overview of what I help implement during a consulting/coaching/fractional engagement:

Goal: create repeatable, scalable processes to move prospects seamlessly through the stages of awareness towards a purchase decision as efficiently as possible.

This entire document is written primarily with the SMB sector in mind, though subscription organizations with sales teams need structure and strategy to sell to enterprise level clients. Enterprise level sales organizations also require highly targeted outbound efforts which are not covered below, though I am happy to discuss on an individual basis. Most of the strategies below can be applied with varying levels of automation, absent a dedicated sales team and/or for lower tier clients.

  • With few exceptions, when prospects first find out about a product through the marketing department’s efforts, they are not ready or able to make the right purchase decision. The solution: a multi-channel lead nurture campaign that meets a prospect in the appropriate stage of awareness and moves them toward certain predetermined engagement milestones so they can be classified as an SQL (sales qualified lead) or disqualified from the funnel. SQLs are successfully handed off to SDRs for further vetting, or directly to sales account representatives.
  • SDRs take additional, predetermined steps to qualify or disqualify a lead before handing off to a sales rep.
  • Throughout the lead nurture process, the company promotes the most valuable aspects of their offering, testimonials from current subscribers, compelling statistics (social proof), and corresponding calls to action that take the prospect to the next step on the customer journey and therefore, closer to a purchase decision. -Foundational desires (peace of mind, respect, elevated social status, etc.) should be used as sales anchors.
  • The most valuable aspects of the company’s offering should be presented as they relate to the outcomes the prospective customer can expect to receive/achieve once they subscribe.
  • Managing appropriate expectations is critical throughout all stages of awareness. Underpromise, overdeliver, and then delight customers. Overpromising in marketing campaigns and underdelivering with new customers is inexcusable for companies that rely on a recurring revenue and is a significant contributor to sub 90 day churn rates.
  • Social media retargeting campaigns coupled with an email lead nurture sequence, on-site live chats, and direct contact from a sales rep is a common multi-channel mix for the SMB market. It’s imperative that retargeting ads and messaging from the sales rep match the messaging of the email nurture sequence.
  • Tune into the prospect’s stage of awareness as they receive an email lead nurture sequence, retargeting ads, and contact from sales reps.

How I define stages of awareness (adapted from Joanna Wiebe of Copyhackers):


A person who fits a company’s ICP but is not aware that the company exists or the problem it can help them solve.

Solution Aware

The prospect is aware they have a problem and that the company exists. The prospect might download a lead magnet at this stage as they move toward active consideration of possible solutions to their problem. Marketing should move a prospect from Unaware —> Solution Aware —> Product Aware or from Solution Aware —> Product Aware before passing the prospect on to a sales rep (or an SDR).

Product Aware

The prospect is now actively considering the available options to solve their problem and could be considered a lead. They are receiving a carefully planned lead nurture campaign. A lead is moving toward Most Aware when they are engaging with your nurture campaign (opening emails, clicking links in emails or retargeting ads, visiting the company’s website, downloading additional content marketing assets, chatting with a rep via on site chat, talking to a rep on the phone or via text, and/or responding to emails from sales). Leads should be transferred from SDRs to sales reps at this stage. Unqualified prospects should be disqualified from being a “lead” at this stage and put on a long term lead nurture campaign.

Most Aware

(High intent to purchase) – The prospect is now a hot lead, ready to pay for the solution they believe will best solve their problem and are showing clear buying signals for the product – those signals should mirror the actions that current Power Users took when they were considering making a purchase. Through the nurture campaign, the lead should have been told the story of why the company’s offering will solve their problem (backed up with social proof) and then asked for action (free trial, attend a webinar, purchase offering, get on the phone with sales, etc.).

  • The overarching goal of a nurture campaign is to move the most qualified prospects to Most Aware as quickly as possible, customize the deal as necessary/applicable, then close the deal. Simultaneously, the campaign should move unqualified leads out of the sales pipeline as quickly as possible.
  • Throughout the nurture campaign the most useful features of the offering must be explained in a way that conveys a clear benefit to the prospect (while setting proper expectations for outcomes/results), and again, speaks to the prospect’s foundational desires. All claims of outcomes/results should be substantiated with social proof (case studies, testimonials, relevant statistics).
  • Objections should be seamlessly managed throughout the lead nurture process, with common objections being strategically handled through social proof in an automated lead nurture campaign before the prospect brings up their objection(s) to the sales rep. When further objections surface, skilled sales staff should be able to launch a mini-discovery process to astutely uncover and address the root objection and move the lead forward in the sales process. Alternatively, at this stage, sales staff should be able to quickly disqualify a lead and refer them to a better suited solution when appropriate.
  • Sales reps should guide the lead throughout the buying process, and the lead should know exactly what happens at each stage of the buying process before it happens. There should be no surprises unless they are hugely positive and for the express purpose of delighting the lead.
  • The Head of Sales must create and refine repeatable, scalable sales processes and ensure that the entire sales team is implementing those processes with precision and great attention to detail. This includes full implementation of a CRM tool that best suits the company’s needs.

Sales must clearly and consistently communicate with:

  • Marketing, to determine the parameters and definition of a sales qualified lead (SQLs) and how & when to hand-off prospects to SDRs or sales reps.
  • Product, to have an in depth understand of the product, feature roadmap, etc.
  • Customer Success, to best understand the ongoing customer journey of power users so they can best identify those leads with the highest LTV potential, anticipate objections, and shorten the sales cycle.

Customer Success

Customer Success systems are the means by which companies help their customers achieve the success the company advertised and play a central role in maximizing cLTV.

Companies start setting expectations of what outcomes their prospects can expect from their solution with the first marketing touch. Sales teams skillfully craft a tailored solution based on the specific outcomes the prospect identifies. Now it’s time for Customer Success to pave the way for new subscribers to achieve those outcomes and feel successful as fast as possible.

Proper expectation setting, creating a culture of feedback, effective onboarding, using customer service tools, keeping tabs on customer engagement, and proper off-boarding are foundational to Customer Success.

**Harvard Business Review tells us that it costs between 5 and 25 times as much to acquire a new customer as it does to keep an existing one. Customer Success should be a top priority in a recurring revenue organization. **

Creating SOPs for every piece of the customer success puzzle for maximum efficiency, scalability, and team member onboarding is imperative.

Customer Success must set up automated processes throughout customer onboarding and ongoing management to truly deliver on the promises made to new customers at scale.

Customer Success KPIs for online subscription based businesses: cLTV, CRC (customer retention cost), churn rate (and/or retention rate), ARR(annual recurring revenue), MRR(monthly recurring revenue), ARPU(average revenue per user), and upsell percentage.

  1. Creating a culture of feedback

The overarching theme of ongoing customer success is to create a culture where feedback is not only accepted, but carefully considered and when appropriate, acted upon. The company must set the expectation during the onboarding process that helpful staff members are just an email, online chat, PM, or a phone call away to help remove roadblocks to a customer’s success. Reinforce that attitude through online community interactions, retargeting ads, and on a one-on-one basis.

Customers of recurring revenue businesses make the decision to “buy” every single renewal period and must continuously derive value from the product. It’s important to remind subscribers how amazing the product and the company are and of the success the customer is achieving.

Surveying current customers one to two times per year is absolutely necessary. This furthers the culture of feedback and will undoubtedly unearth useful information that will improve organizational decision making. Survey different segments of subscribers based on their engagement level with the product. Ask Power Users different questions than segments who are least engaged. More on the tech required for proper customer segmentation and hyper-personalized engagement tracking in the Engagement Tracking section below.

  1. Onboarding

Onboarding is the process of taking a brand new subscriber, beginning at sign up, on the fastest path to value recognition, and over time nudging them along the path to becoming a Power User. Onboarding is a key fixture of a long term retention strategy.

The onboarding experience should mirror the messaging a prospect received during the lead nurture campaign and promises made by Sales. In other words, the expectations set during marketing & lead nurture should be met and exceeded once the prospect buys: underpromise, overdeliver. Do that by explaining how the new customer can fully benefit from each and every aspect advertised about the product in an intuitive way through a combination of email, on-site feature tours, in-app messaging, videos, in-app pop-ups, and more.

The effectiveness of onboarding should be measured and tested, just like marketing campaigns.

Customize the onboarding process if possible/necessary by allowing new customers to self-select their top priorities & desired outcomes with the product. Marketing should have explained the “what” and “why” of the product’s features, the onboarding process should explain the “how” to use each feature and receive its full benefit/outcome.

Since the goal of onboarding is to take a brand new customer on the fastest path to value recognition, and over time nudge them along the path to become a Power User, you need to know what steps current Power Users have taken in the past to achieve power user status, and strategically send new customers on that same journey.

  1. Engagement Tracking

Engagement tracking simply means understanding and keeping tabs on how customers are interacting (or not!) with the product and then taking appropriate action to either bring a disengaged subscriber back into participation and value recognition, or conversely, to offer the most engaged subscribers relevant, useful, upsells to maximize their cLTV.

The path to maximizing profitability in a recurring revenue based business is not just acquiring new customer, but keeping track of who is most and least engaged, and then doing something about it.

Get the technology necessary in place to accurately tag and segment customers based on engagement, usage, or however a company measures value recognition. [Intercom] is one of the top tools available for hyper-personalized onboarding, engagement tracking, user segmentation, and in-app messaging. They allow online companies to send the right message, to the right person, at the right time.

Once a tracking tool is in place, a process document that explains in detail what actions need to be taken based on engagement tracking information should be created and implemented.

If a customer success team doesn’t have visibility into engagement metrics and SOPs for how to interpret and take action on that data, there is no clear path to maximizing cLTV.

There are 2 primary scenarios to prepare for in this particular SOP: how to bring disengaged subscribers back into active participation and value recognition, and second, how to offer appropriate upsells to the most engaged subscribers (Power Users).

Relentlessly track engagement metrics and the results of re-engagement and upsell campaigns. If we take Harvard Business Review’s retention stats seriously (that it costs 5 to 25 times as much to bring on a new customer as it does to retain an existing one), subscription organizations should be paying an order of magnitude more attention and care to engagement metrics than marketing metrics.

Those subscriber segments that are most engaged should be offered appropriate upsell opportunities for tangential products or services, for example: a higher tier subscription with more benefits, access to a mastermind, a tangential product, a cross-sell offer that results in an affiliate fee for the company, etc.

New customer acquisition in a subscription business is certainly of high importance, but retention is mission critical. If new subscribers are jumping ship early on, either Marketing & Sales are bringing in the wrong subscribers, Customer Success is asleep on the job, or the Product is subpar. Fix your leaky bucket.

  1. Community

A carefully curated online community can be one of the most effective retention strategies to employ for an online recurring revenue business.

Often on a membership website, members join for the content, but end up sticking around because of the community. Some type of group interaction in the form of an online discussion forum or Facebook Group can be the differentiator between a membership site where people show up, consume the content, and churn before the 90 day mark, versus those who stay for many months or even years because of the value and relationships they are receiving from that group interaction.

SaaS and subscription based businesses can also enjoy the benefits of an online community. Granted, an online community is not valuable and appropriate in every scenario, but that’s often the exception rather than the rule.

At the outset, running an online community requires a great deal of intentionality, time, and cultivation. Starting a community is not a decision that should be taken lightly, but when done well, the benefits far outweigh the costs.

To begin, cast a vision for what a successful community would look given the company’s type of customers + offering, and work backwards to create a strategy for bringing that vision to life. What platform would be best to use? What kinds of discussions would happen there? How will participants get the most value from it? What does a “successful” community look like in this niche?

As with every part of running a recurring revenue business, proper expectation setting from the outset is necessary. Marketing campaigns should reflect the community accurately. Hopefully that means a kind, welcoming, helpful bunch of people who are invested in each other’s success. Then, during the onboarding process, make sure the community’s rules and guidelines are agreed upon by the new group member before they can interact with others.

On an ongoing basis, its Customer Success’ responsibility to enforce those rules (through contributors & moderators) and cultivate a community that reflects the vision cast for it from the beginning.

  1. Customer Service

Customer service generally boils down to problem solving with current customers. As with every other area of customer success, dedicated staff members should “own” the customer service department.

Using a purpose built tool for support tickets and the overall customer service experience is hugely important with regard to systems, processes, automation, and delegation. SMBs relying on an email account or spreadsheet to manage support tickets is insufficient, unscalable, and unprofessional.

Whenever speaking with a customer, reps must have empathy, show kindness, apologize when necessary, and be solution oriented. The “voice” and tone of customer service reps should reflect the overall company persona.

Reps should have dedicated SOPs for handling common problems, following up, and feedback loops, as well as clear directives on when and how to escalate a support ticket.

When customer are upset, treat that as an opportunity to delight them – think How to Win Friends & Influence People! If that subscriber’s experience is so overwhelmingly positive when they approach customer service for help, research shows that they will actually be a happier customer than before they had the problem.

  1. Off-boarding

Often overlooked, proper off-boarding of subscribers is essential for recurring revenue businesses to best understand the customer journey. Companies must understand the reasons their subscribers leave, identify off-ramps, and make adjustments in every relevant area of the revenue funnel (Marketing, Sales, Customer Success/retention) to lower churn.

The decision for a customer to cancel should be very difficult, whereas the process to do so should be simple and straightforward. The exit should not be under heavy guard or hard to find. An automated exit survey should be in place and Customer Success should be in charge of instigating action based on those replies.

Subscribers should be given the option to downgrade or pause their account, asked why they’re cancelling on one screen and given a corresponding “fix” offer on the next in an attempt to “save” the customer. If you have the staff for it, a manned chat bot embedded in cancellation related pages can be an effective tool to aid retention and better understand customers.

Product (content for memberships & subscriptions; physical product for sub boxes; software for SaaS)

Bottom line: Set accurate expectations – beginning with the very first marketing touch – of what customers can expect to get when they’re learning about the company’s product or service and what it has to offer. If prospects are told exactly what to expect and they indicate they’re good with that, (by making the purchase…) the relationship is off to a great start!

Underpromise, overdeliver + delight = Power Users.

Miscommunication about product functionality, delivery dates, feature roadmaps, upcoming content, etc. is the source of much internal consternation in any online recurring revenue business. The Head of Product should take great pains to communicate effectively with Marketing, Sales, and Customer Success to ensure consistent messaging on an ongoing basis.

Bridging communication gaps between Product and all other departments is foundational to a successful recurring revenue business. Creating & successfully implementing SOPs for how this will be handled is key for each of my consulting engagements.

I believe in value-based pricing, which can take many forms. I help my clients determine key value metrics and develop appropriate pricing strategies and ways to test them. Pricing & upsell strategy should be an ever-evolving practice in a recurring revenue business and tested constantly.

Wrapping Up

Running a scalable subscription-based company is tough. It’s inherently more complex than the single-sale ownership model and requires a unique toolkit. If you’re firing on all cylinders and have already implemented everything above, good on you! – pass this to a friend who needs a nudge in the right direction.

My consulting methodology is a holistic approach that produces measurable results and creates a foundation from which to scale an online recurring revenue business.

Seventeen years of sales experience, consulting work in a variety of industries, and a relentless pursuit to continuously improve my business skills has given me a knack for incisively identifying problems and designing effective solutions for my clients.

Request a free 60-minute strategy call now and set your subscription company on a path to scaling, profitability, and organizational health!

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