Enterprise Onboarding in 2024: Key Takeaways From Our Discussion

Enterprise Onboarding in 2024

In this conversation our co-host Walter Chen sat down with ​​Markus Rentsch, CEO @ Remark-able, ​​Conor McCarter, Co-Founder @ Prequel, and ​Daniel Zarick CEO @ Arrows to break down what it takes to successfully sell to and onboard enterprise clients in 2024. They cover everything from the increasing demands of enterprise customers to the importance of good onboarding and customer success. The discussion is a practical look at how startups are stepping up to the plate to meet the needs of large organizations, and why it's critical to stay flexible, collaborative, and focused on delivering value from day one.

1. Selling to enterprises is no longer off-limits for startups
Gone are the days when selling to big enterprises was something only seasoned sales teams could handle. Startups now feel empowered to go after enterprise clients right from the start, even without a formal enterprise sales background. The tools and resources available today allow startups to approach large clients confidently and successfully. What’s interesting is that it’s not just about having a sales team that knows how to talk the talk—it’s about creating real value that big companies need. Startups that can solve major problems for enterprises, no matter their size, are getting their foot in the door faster than ever.

2. The table stakes for enterprise sales keep growing
If you want to sell to enterprises, the bar just keeps getting higher. It’s not enough to have a good product anymore—you need to tick off a long list of “must-haves” to even get a foot in the door. Things like SOC 2 compliance, SSO, and data integration are now non-negotiables. Where startups used to get by with a little flexibility, enterprise customers now expect security and features that were once reserved for only the most advanced players. It’s almost like playing in a high-stakes game where the requirements keep stacking up. Startups that can keep up with these growing demands, though, are going to have a huge edge because enterprise customers aren’t messing around when it comes to security and compliance.

3. Customer onboarding is a crucial first impression
You’ve heard it before, but it’s worth repeating: you only get one chance to make a first impression, and in enterprise onboarding, that first impression can make or break the relationship. Enterprises are sophisticated customers who expect things to go smoothly, and they won’t stick around if they hit roadblocks early on. If your onboarding process is disorganized, slow, or unclear, you’re setting the tone for the rest of the relationship—and not in a good way. On the flip side, when onboarding is seamless, it builds immediate trust and positions your startup as a reliable partner. This isn’t just about showing them the ropes—it’s about demonstrating that you’ve got your act together and can deliver value right from the start.

4. Customer success starts from day one
A lot of people treat customer success as something that kicks in after a product has been fully integrated and used for a while, but that’s not how it works anymore—at least not if you want to keep your enterprise clients. Customer success begins the moment you sign the contract. Every step of the onboarding process contributes to whether or not that client is going to stay happy and stick around. Think of onboarding as an extension of the sales process. Just because the paperwork is signed doesn’t mean you can sit back and relax. The real work begins when you start delivering on the promises you made during the sales pitch. If you’re not setting your clients up for success from the start, you’re leaving a lot of money on the table when renewal time comes around.

5. Startups are evolving to sell like enterprises—and vice versa
It’s fascinating to see the overlap happening between how startups and enterprises operate. Startups are becoming more sophisticated in how they sell, while enterprises are adopting some of the lean, agile methods that startups have been known for. This crossover means that both sides are starting to speak the same language, making it easier for startups to land enterprise deals. Enterprises are more willing to take a chance on smaller players because they’re seeing that startups can be just as capable of delivering the solutions they need. At the same time, startups are learning that scaling means adopting more structured processes, like those found in large organizations, to keep up with the demands of big customers.

6. Processes are critical, but flexibility is key
There’s no denying the importance of having solid processes in place, especially when you’re dealing with enterprise clients. But here’s the catch: you’ve got to stay flexible. Large enterprises move at their own pace, and if your processes are too rigid, you’re going to hit roadblocks. The companies that win in this space are the ones that can adapt to their clients’ needs, whether that means creating custom solutions or tweaking the way things get done. Flexibility doesn’t mean abandoning your processes; it means being able to adjust when necessary to keep the customer happy and ensure a smooth experience. It’s a balancing act between staying structured and knowing when to bend the rules.

7. Enterprise deals require heavy lifting
Everyone loves the idea of landing a big enterprise deal, but the reality is that these deals often come with a lot of extra work. Unlike smaller clients, where you might be able to hand off a product and let them figure it out, enterprise clients often need more support—and sometimes that means rolling up your sleeves and doing more than you initially expected. It could mean building out custom features, offering more one-on-one guidance, or simply spending more time smoothing over the onboarding process. But here’s the thing: while this heavy lifting might be a short-term pain, the long-term rewards can be massive. Enterprise clients bring stability and growth opportunities that are worth the extra effort.

8. Renewals have to be earned, not assumed
It’s tempting to think that once you’ve signed a client, the hard part is over. But if you’re not constantly proving your value, you’ll find yourself scrambling when renewal time comes around. Renewals aren’t automatic—you’ve got to earn them. It’s not just about delivering on what you promised during the sales process; it’s about staying engaged with your customers and making sure they’re getting the value they expect. Avoiding tough conversations or hoping a client won’t notice if something’s off isn’t a strategy—it’s a surefire way to lose them. The best approach is to stay proactive, address any issues head-on, and constantly demonstrate that your product is essential to their success.

9. Onboarding should be a team effort
Onboarding isn’t a solo mission. It requires a well-coordinated effort from sales, customer success, product development, and often the engineering team. Each of these groups plays a crucial role in making sure the client is set up properly and starts seeing value right away. When any part of the team isn’t on the same page, things can quickly go south, and that’s a risk you can’t afford with enterprise clients. By collaborating and keeping the lines of communication open between teams, you ensure that the onboarding process goes smoothly, setting the client up for success right from the start. It’s about making sure that every team member understands their role in the customer’s journey.

10. Data export and integration are game changers
When it comes to enterprise clients, data is everything. These companies have massive amounts of data, and they need to be able to move it around seamlessly. That’s where data export and integration become make-or-break features. Startups that can offer smooth integration with tools like data warehouses (think Snowflake or BigQuery) are going to be in a much stronger position to win enterprise deals. Being able to give your customers the ability to export and manage their data easily makes your product stickier and far more valuable. If you can’t offer these features, enterprise clients are likely to look elsewhere.

Larger Takeaway

The big picture here is that landing enterprise deals is about more than just having a great product—it’s about proving you can handle the complexity that comes with working with large organizations. From meeting higher security and compliance standards to delivering seamless onboarding and customer success, startups that want to compete in the enterprise space need to be prepared for the long game. It’s not easy, but the reward is worth it. With the right combination of flexibility, collaboration, and value-driven processes, startups can turn enterprise clients into long-term partners that help them

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