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How do you effectively transition away from founder-led sales and scale your sales motion? Lessons from a 2x exited founder and a Series B founder

November 28, 2023

Ah, founder-led sales. It’s how every company starts out with selling.

But we can’t rely on it forever. You’ll need to transition away from founder-led sales to keep building up momentum and growth. 

  • Founders, you’ve found your product-market fit and got a steady stream of customers already, Now, it’s time to carve out time to focus on other areas of the business.

It’s always a tough process, and you can make a lot of painful mistakes along the way. So how do you do it right?

For the second edition of the Asia Growth Podcast Startup Special series, we’re delving into some tough lessons on transitioning out of founder-led sales and leveling up your sales motion post-PMF.

Jeremy Au (VC, Monk’s Hill Ventures and Host, BRAVE Podcast) interviews Grace Sai (CEO and co-founder of Unravel Carbon) and Ajay Bulusu (CEO and co-founder of NextBillion.ai)

  • Monk’s Hill is an early-stage investor in Southeast Asia, mainly investing at Pre-Series A and Series A. Before joining Monk’s Hill, Jeremy built and exited his own startup in the US.
  • Grace is a 2x exited founder whose latest venture, Unravel Carbon, raised the largest seed funding for a climate tech startup in Asia last year. 
  • Ajay has held leadership positions at Google, Grab, and Indeed. NextBillion.ai raised a $21M Series B last year. 

Here are their hard-earned lessons, so you can transition out of founder-led sales smarter:

1. Know when it’s the right time to transition.

Ajay shares that the transition away from founder-led sales begins when you hit some form of product-market fit (PMF) and it’s clear that the founder-led sales motion is working.

  • The signs:  At this stage, you’re likely closing deals and seeing consistent (and recurring) clients for a few months. 

For 2x exited founder Grace, her role as a founder was clear from the start:

“Having [built and scaled startups] a few times now, I was very clear that that was my only duty in the first 18 months. When we saw the signs of PMF. That was the first time that we hired a commercial team. So for 18 months, it was purely founder-led."

The danger of stepping away too early. Stepping away from founder-led sales too early can be an expensive mistake—and it’s common. Even Ajay has made it. He shares:

“The biggest mistake I made was to step away from sales too early. We had raised a lot of money and were first-time founders. Some elders advised us and said, listen, go hire a VP of sales, go hire a director of sales. We burnt a lot of money hiring.”

Making the transition too fast too soon can make you miss out on critical customer context and trends. Founders need to stay on top of these insights to maintain a competitive edge. 

2. Stay involved during and after the transition.

But how do you continue gaining these insights even after transitioning away from founder-led sales? Staying involved—even in small ways. 

Here’s how Grace and Ajay do it:

  • Grace and her co-founder are in every customer channel, personally attend onboarding sessions, and even lead 4 to 5 sales calls a week!
  • Ajay and his co-founder also lead around 6 customer calls a week, and listen to more than 16 call recordings stored in their customer relationship management (CRM) platform, HubSpot

As a founder, you’re the one with the most insights and broader context of the business, as well as the product you sell. That’s why you can’t completely step away from sales.

Ajay still coaches his salespeople today, especially because his company sells niche technical products.

  • He trains his staff on their sales pitch to make sure they aren’t undercutting their prices and selling the service short. 

3. Structure your sales team based on what your startup needs.

There’s no one-size-fits-all way to structure your sales team. Ajay and Grace both have different stories on how they structured their teams. 

  • Why the difference? It’s usually because of the product and the industry you’re in. 

Team size. Right now, Ajay has 4 account executives (AEs) reporting to him as a Series B startup, while Grace has a 9 person commercial team at the seed stage.

  • So…why only have 4 AEs in Series B? It’s partly because Ajay’s products are more self-serve. Unlike other startups, he doesn’t need to sell aggressively to all customers.

Who’s part of the team? In Grace’s case, she’s in a B2B climatetech/deeptech industry.

For her, the main choice was between hiring a very experienced B2B salesperson who has carried and achieved 1M quotas and would pay for themselves 10x and then train them on sustainability topics or hiring ex-sustainability consultants and training them on sales.

  • She did both. Now, she’s seen success in flanking a very experienced B2B salesperson with a sustainability consultant.

When to hire a sales leader? Another common piece of advice shared by founders is not to hire a sales leader too early. 

While Grace believes in hiring a sales leader slightly earlier, she isn’t hiring the sales leader to craft the sales playbook, train the first AEs, and completely delegate sales over to them.

  • One reason she hired them earlier is because two of the three key metrics they track for PMF are sales metrics. They need to set up the processes (sales ops) required to collect, track, and analyze sales metrics clearly and regularly. That’s why she looked to hire a Sales Director who is good at both sales and sales ops. 

4. Finding the right hire for a growing team.

What makes founder-led sales work is the founder’s deep product knowledge and raw passion to succeed. And that kind of energy may be hard to replicate. Jeremy put it best: 

“Founders succeed in sales due to their passion, deep product understanding, and hard work. However, this success may not be based on a scalable and repeatable sales process.” 

It’s not about seniority. Don’t be too quick to hire a very senior salesperson and pat yourself on the back. Ask yourself if that’s what you really need at an early-stage startup. In reality, you need someone who is used to closing deals. As Ajay puts it “When you hire a very Senior Salesperson, he/she is used to managing revenue, they probably haven’t sold directly in a long time.”

The “obvious” hire may not be the best. In Ajay’s case, mapping is an old-school business. So, most of the salespeople (with mapping experience) that they get are from the previous generation of sales.

  • What they’ve done is go to AWS or GCP and hire a cloud salesperson instead of a map salesperson because they are used to selling similar infrastructure products.

Training your team for the long haul. Search far and wide, and you’ll still have trouble looking for the perfect candidate with the perfect background and perfect experience. You’ve got to give them some love and training. 

  • Grace and her co-founder would roleplay potential clients and ask tough/difficult questions to prepare new salespeople for calls. Ajay’s team would even give easier-to-handle clients to junior salespeople for that hands-on experience. 

5. Leverage the right tools to enable your sales motion.

The tools you’ll be using depend on the metrics you are looking at and what works best for your team. Grace’s team uses HubSpot because it offers them a single source of truth. It also integrates with the rest of their sales stack, including tools like Apollo for lead generation and Aircall for outgoing calls.

“We use HubSpot to run our end-to-end sales motion, encompassing everything from lead qualification and deal tracking to reporting. And we need to analyze a lot of things because we measure PMF through three metrics: sales cycle, Average Contract Value (ACV), and customer love."
"Two out of these three metrics are driven by sales data. We need to look at the data religiously. So we go through the data every week.”

6. Compensation, bonuses, and motivation.

On compensation. If you’re still in the early stage, you want to make sure that you’re using your money wisely while compensating your sales team fairly. Grace believes that founders should work backward to define their compensation based on their targets. She shares: 

“Let's say a hundred grand a year in Singapore, that would be just 50% of the total comp, so the other 50% is their target earnings. Then their quota is 10x the base salary or 5x the overall.'"
If they're paid 100,000, their quota or what they need to achieve is 1 million a year. So in that sense, it's very binary.”

On bonuses. Meanwhile, Ajay believes in being generous to their first few salespeople in terms of commission, so they feel encouraged to stay with an early-stage startup. If they closed a $100K deal, he’s okay with giving them $10K, even if it’s a referral.

  • But incentivizing bookings? That’s his no-no. Your bookings will not guarantee a sale, so you have to incentivize people on invoices.

How to boost morale. Grace and Ajay run internal metric-based competitions for their sales teams with relevant rewards that excite them. 

The VC lowdown

For Jeremy, transitioning to founder-led sales is divided into three core chapters. 

The first is developing a repeatable sales process, saying that "The best founders are intentional in documenting their personal sales process from end-to-end.” 

They often bring in a junior salesperson to help support the definitions of the sales stages, customer personas, leading indicators, and more.

Next is hiring the right talent, where he advises founders to find sales leaders who have products with similar pricing and consideration processes. Don't be afraid to poach from benchmark startups that are several years more mature than your company. Keep an eye out for high initiative, hunger, and cadence of work.

Finally, he believes founders should heavily invest in onboarding. 

“The founder has to continue the sales meetings with the new joiner shadowing and gradually running the process with new logos.” 

There should be a mutually agreed probation period where either party can choose to walk away.

At the end of the day, making a successful transition away from founder-led sales will look different for every founder. But we hope that some of these insights and experiences will be helpful for founders making the transition today. 

This is part two of the Startup Sales Masterclass Series by HubSpot for Startups. These insights were extracted from the Asia Growth Forecast, a podcast where they decode successful sales strategies of fast-growing brands and show you how to scale your business in Asia.

BackScoop is teaming up with HubSpot to bring the best actionable tips from their three-part Asia Growth Forecast Startup Special to our audience of startup operators. 

Their program, HubSpot for Startups, helps entrepreneurs scale their businesses and is on a mission to help millions of startups grow better.

Want the right set of tools to transform and scale your sales strategy? You can get access to free masterclasses, startup toolkits, a connected ecosystem, and up to 90% discount on the entire HubSpot platform here. (Don’t forget to select Bootstrap Asia as your partner when applying.)

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