The overlooked art of customer onboarding

There's more to customer success than just getting them to sign - let's unpack successful customer onboarding.

Hey, Aaron here! Welcome to this bimonthly startup newsletter. In each write-up, I tackle questions about building products, financial planning, growth, and raising capital! Today we dive into -

Education: How to conduct market research

Opinion: The overlooked art of customer onboarding

Notable News: Salesforce buys Informatica, you can now talk to Claude, and Circle hopes for a multi-billion dollar valuation.

Education:

How to conduct market research as a founder

Opinion:

The overlooked art of customer onboarding

Early-stage founders spend so much time building and selling products that they often forget the work isn't done once a customer signs. It's (fortunately & unfortunately) only just beginning.

If you’re unable to get customers up and running quickly, easily, and in a way that fits how they operate, you’re not scaling your business, you’re just bottlenecking your own success. “Closing” customers only looks like the win; the real win is onboarding those customers and working to deliver a consistently positive experience. This drives retention, this drives use, this drives success.

Build Systems for the Stage You’re In — Not for the Fantasy

One of the most common mistakes founders make is overbuilding for a future that does not exist (yet). They set up complex automations, sophisticated CRM flows, endless backend systems — all designed to manage thousands of leads when they haven’t collected 100 in total. This is about scaling systems in response to demand, not in advance of it. It may hurt you a bit when you feel your Google Sheets-based CRM struggling under the weight of going from 1 new lead per day to 10, 30, and now 50. Let the time you’re investing in doing something manually teach you exactly what needs improvement in order to scale. Scale what you know works, not what you think works.

Here's a simple system improvement framework that I use myself. Our goal is to get to Level 5 by going step by step through Levels 1, 2, and 4.

  • Level 1: Fully manual sales/onboarding with notably poor efficiency (everything is a pain, and you’re learning nonstop). This would be where I’m using Google Sheets as a CRM.

  • Level 2: Onboarding supported by basic systems and initial high-level documentation — SOPs, templates, clear processes to move faster. This is where I’d transition to a free/cheap CRM like HubSpot to cover the basics.

  • Level 3: We skip level 3 in any Unconventional Ventures-related scale since this score doesn’t let us know if something is a little better/worse or higher/lower on the priority list. As business owners, you need to make business decisions based on business intelligence, and if everything in the organization is rated a 3/5…well, that’s the opposite of business intelligence, I’d say. 

  • Level 4: Highly Tech-enabled — utilizing automations, onboarding “wizards”, and highly standardized sales/onboarding materials to sell and onboard as fast as what we’ve learned from Level 2 will allow us. This is where I’m using a lot of HubSpot features and connecting/integrating with other software, both third-party and potentially my own.

  • Level 5: Fully automated sales/onboarding or near-perfect manual efficiency where automation isn’t realistic. As good as you can make it. For B2C, it could be creating a sales process that allows you to create an account and onboard within 5 clicks. For B2B, this could be you lowering the time to onboarding from 3 months to 3 weeks. Whatever allows you to be high on the efficiency curve without sacrificing quality. Note: Most founders will sell their companies at Level 4 or between 4/5.

Most startups make the mistake of trying to leap straight from Level 1 to Level 4 or 5 without ever mastering Level 2. They build sophisticated bridges when they barely have any traffic on the roads, wasting time, money, and focus. Rather than do this, we encourage our clients/ourselves to take it step by step. To note, it’s completely fine to move through the levels as quickly as possible, we simply encourage you not to skip levels as each one provides learnings that enable efficient and consistent growth.

At Level 1 we learn what the customer likes/wants, focusing on providing a white glove/manual servicing as necessary, at Level 2 we make providing those initial needs/wants easier for them to experience and for us to deliver, at Level 4 we find ways to make what’s working work better with an emphasis on maintaining the customer experience, and finally Level 5 focuses on maximizing efficiency while again, never losing sight of maintaining the customer experience.

Punchline: Master manual first. Systematize second. Automate third.

Build Around the Customer, Not Yourself

Especially before you’re doing $1-3mm per year in revenue, sales and onboarding flows should be tailored around what makes life easier for the customer, not what makes life easier for the founder.

If your customer wants to export an Excel file and send it to you because that’s the fastest/best experience for them, you shouldn’t push them to use a complicated portal or reformat all their data. You make it work. Or better yet, you find an even easier way for them to engage.

Every extra hurdle you put between a customer and value is an invisible tax on your growth.

B2C businesses see this when, as an example, a user abandons signing up because they were forced to fill out an onboarding form with 30 questions instead of being able to register with their Google account. B2B companies feel this when, as an example, prospects bail out of a long and complicated onboarding process because it was too much of a lift on the customer’s tech team.

Efficiency + Customer Satisfaction = Real Scale

The goal is never just operational efficiency for its own sake — and it’s not customer satisfaction at the cost of chaos either. It’s both. Part of the founder journey is learning to balance competing forces, be it investors vs. cofounders, seniors vs. juniors, or speed vs. quality, etc.

  • Internal efficiency: set up the company to deliver at a consistently high quality.

  • External satisfaction: make sure customers like the offering enough to stick around.

Early on, customer experience takes priority because you’re still proving that you deserve their loyalty. Remember, they don’t know you. You are a stranger, and just because you trust you doesn’t mean they do. In due time, you can build both brand loyalty and the internal operations to scale without breaking (too many) things — but you won’t have that chance if you lose all your customers because you focused more on the future of the product instead of the present of the customer.

Every business is different, but the principle stays the same: Make it easy. Make it fast. Make it customer-first.

My Takeaways / Next Steps (if I’m a first-time founder)

  • Plan sales/onboarding around what customers find easiest, not what you prefer.

  • Build systems for 3-6 months ahead, not 24.

  • Move from manual (Level 1) to manual + efficient systems (Level 2) before even thinking about fancy tech/automations (Level 4/5).

  • Relentlessly audit sales/onboarding friction. Every unnecessary step cuts retention.

Notable News

That’s It For Today!

Written By Aaron @(un)conventional Team