Scaling Your Startup 10x From $20M to $200M with Sapphire, Lightspeed, TripActions’ CRO, and 6Sense’s CMO (Pod 522 + Video)

When you think of scaling up, many things may come to mind, like hiring, culture, marketing, and sales. But what are the essentials of scaling up, and how do you navigate obstacles along the way to function as a high-impact organization?

Cathy Gao, Partner at Sapphire Ventures, and Anoushka Vaswani, Partner at Lightspeed Venture Partners, moderated a panel with Carlos Delatorre, CRO at TripActions, and Latané Conant, CMO at 6sense to discuss how you can scale your startup from $20 million ARR to $200 million ARR through go-to-market execution, talent, and culture.

The go-to-market playbook

Going from $20 million to $200 million can be tricky, especially since many strategies that would’ve worked for you before might need significant changes or adjustments now. Recalling how Latané operated when 6sense was scaling up, she says:

Before $20 million, your workforce is in beast mode, where everybody does everything and you’re building your team with swiss army knives to reach your mark. When you get to $20 million, you grow your team with dedicated specialists.

Here are three things that helped 6sense reach this mark and beyond:

  1. Defining their revenue operating model by hiring for RevOps and not taking the common DevOps and SalesOps approach. This model worked backward into pipeline quotas which defined how much revenue they needed to create every week, month, and quarter. The go-to-market segment worked together on key metrics across the revenue board.
  2. Building an outbound motion that captures demand efficiently. For this, they made their BDRs laser-focused on behavior-based signals, ICP, and recurring processes to help them become account executives. 
  3. Never thinking small and instead made decisions that were bold and audacious for a company of their revenue size. This helped them break out of the noise and keep away from play-it-safe strategies.

According to Carlos, you don’t go from $20 million to $200 million with a great product alone or a sexy demo. You need repeatability based on a strong foundation. This foundation has three pillars:

  1. Recruiting: You need to have clarity on the profile of a successful account executive and how you’ll identify them, quickly assess them, and retain the exceptional talent in your organization.
  2. Skilled development and enablement: You can’t disrupt a market by hiring people from legacy vendors hoping they’ll figure it out. You need people with fresh thinking, especially sales athletes and leaders who know your market. Once you hire them, you need to train and enable them to become even more talented sales professionals with knowledge about databases and expense management.
  3. Execution: If you have great performers and an excellent training program, you need a robust implementation framework to bring all of it together. This includes pipeline generation, champion building, and qualification.

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Does PLG really help scale by a large amount?

To get from $20 million to $200 million, you’ll take bigger deals with huge companies. Here, PLG would come in handy if you’re selling to a smart tech company, and they can easily connect the dots with a great demo or use case. Carlos says:

To scale, you’ll go to companies where decision-makers are involved who may never use the product. You will need to build an agile sales team able to discover pain points, build real value, and sell top-down as well as bottom-up. This has been our key to go up-market and scale at TripActions.

For Latané, a huge part of being a CMO and go-to-market leader is being obsessed with experience—product, sales, customer interaction, and marketing. So, bringing a product experience to the customers in the form of a snack can work tremendously to showcase the product’s true value.

To adopt PLG in your demand motion, you need to offer your audience something more interesting than your generic blog content gated behind a sign-up form to engage them. Here, offering an experience like a calculator or something juicier is an integral part of the modern go-to-market motion.

The friction between sales and marketing

Marketers need to understand that the only asset sales have is time, and they must choose how they spend every second of every day wisely. So, marketing teams should consider the sales team as their most precious and expensive channel.

Marketing teams must separate the most winnable demand signals and focus on the sales velocity model to put the sales team in a position to win and focus their efforts in the right direction. From a marketing perspective, Latané says:

The more sales and marketing can work together to triangulate on a plan that isn’t just quota-built, but market-driven, the better shape we’ll all be in, and the better results it’ll get collectively.

When there’s tension, marketing looks for a metric, and sales externalize the responsibility for the pipeline. From a sales perspective, Carlos says:

Highly functioning executive teams are empathetic of each other. As CRO, if I’m part of a high-functioning team, I have a stronger relationship with the CFO, Head of Product, and the Head of Marketing than I do with my team. This makes us completely aligned with what the company cares about.

Maintaining talent and culture during rapid growth and scaling

As you’re scaling a sales organization, it’s essential to understand who you want to hire. For example, TripActions believes their quota-carrying sales reps should have intangible qualities such as intelligence, drive, grit, coachability, and values, and tangible qualities such as pipeline generation, champion building, and qualification. 

Being clear on the ideal picture of each role will help you build a team with high talent density. If you don’t have great talent or a talent-defining framework, it’ll be challenging to develop a strong culture as you grow and move forward. 

In terms of culture, there should be a greater focus on two-way and peer-to-peer communication in the form of quarterly business reviews and other activities. If you have a talented team with open communication, this can help promote culture.

Organizing mid-year field kickoffs on a large scale where you invite your go-to-market team, along with the sales, can help set the tone for the entire year. 

However, work should always be fun—more than a grind. Latané says:

You should like what you’re doing, how you’re doing it, and with whom you’re doing it. Since your people make the products, it’s important for them to have fun and make your product fun for your customers.

Combatting burnout and maintaining morale during ever-evolving processes

Acknowledging that those on your team have personal lives and are going through hard things on a personal level is important. This doesn’t mean giving Fridays off and calling it a day. Rather, get to know what’s going on with each person on your team and make accommodations on an individual level. Carlos says:

People are most engaged when they’re growing, learning, and winning. TripAction adjusted the meaning of success when the dynamics of culture transitioned. But they were scaling large and quickly. Reforming sales metrics became achievable in the new environment, and the team was no longer under as much pressure.

Key takeaways and final thoughts

You always need to be learning, growing, and challenging yourself and your people in the company. Additionally, you need to think bigger than you are today—if you’re at $10 million, think you’re at $100 million, or if you’re at $100 million, think you’re at $300 million.

Finally, when you’re hiring, slope matters more than scale. For example, a leader who’s been a part of growing a company from $10 million to $40 million may have a better idea of building systems for scale and hiring and managing talent than someone who saw it grow from $80 million to $120 million.

Published on January 28, 2022

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