- Scaling a sales team from startup to enterprise requires rethinking process, tooling, and talent at each growth stage — what works at $1M ARR breaks at $50M.
- Early-stage teams rely on founder-led selling and tribal knowledge; growth-stage teams need repeatable processes, enablement infrastructure, and operational rigor.
- The Wingman-to-Clari journey illustrates how conversation intelligence and revenue intelligence tools evolve from nice-to-have to essential infrastructure.
- AI tools that consolidate knowledge, automate repetitive work, and provide deal-level intelligence become critical at scale — manual processes cannot keep pace with growing pipeline.
- Lessons for sales leaders: invest in infrastructure before you need it, codify tribal knowledge into systems, and adopt AI to scale output without proportionally scaling headcount.
- Scaling a sales team from startup to enterprise requires rethinking process, tooling, and talent at each growth stage — what works at $1M ARR breaks at $50M.
- Early-stage teams rely on founder-led selling and tribal knowledge; growth-stage teams need repeatable processes, enablement infrastructure, and operational rigor.
- The Wingman-to-Clari journey illustrates how conversation intelligence and revenue intelligence tools evolve from nice-to-have to essential infrastructure.
- AI tools that consolidate knowledge, automate repetitive work, and provide deal-level intelligence become critical at scale — manual processes cannot keep pace with growing pipeline.
- Lessons for sales leaders: invest in infrastructure before you need it, codify tribal knowledge into systems, and adopt AI to scale output without proportionally scaling headcount.
A few weeks ago, we had the pleasure of catching up with Shruti Kapoor, Head of International Business at Clari, as part of our flagship video series, "Wintage Club Conversations." Shruti is the founder and CEO of Wingman, which was acquired by Clari in 2022 and she has seen a journey of 5x growth in the last 18 months. She now heads the International Business for Clari across India and APAC. She is passionate about helping revenue teams hit their goals, through better conversations with their customers.
In this blog, we're going to capture some of the highlights from our conversation with Shruti. You can watch the full interview here.
Transitioning from a small team at Wingman to a scaled revenue team at Clari
Shruti noted that while there was definitely an adjustment to be made when moving from managing a small team to a scaled one, the key difference for her was the shift from selling to small businesses or mid-market-sized companies to selling to enterprise customers. There was a lot of learning involved and she made several new observations.
For each enterprise sale, you need an account plan and you have to map out multiple stakeholders, understand what their motivations are, and even where they are in their career. In some cases, Shruti explained that it was also helpful to know how purchasing their product would impact the buyer's growth in the organization and what challenges they might be facing at a role level. Any advantage you can establish with data counts, so the more data you have, the more likely the sale.
GenAI - a great fit for sales
Reflecting on the transformative role of GenAI in sales tools over the past year, Shruti agreed that in a short time frame, it's become a staple; almost as if it had always been part of the landscape. Here are some of the critical ways in which she feels GenAI has revolutionized sales in the last year:
- Data interrogation: The ability to query data directly is a game-changer. Platforms like Hubspot and Salesforce are at the forefront, redefining data analytics and dashboard functionalities. The surprising trend we're seeing with this wave of technology is the rapid adoption across the board from startups to tech giants.
- Enhanced meeting insights: Post-meeting analyses have evolved. Sales professionals can now inquire about anything from specific customer reactions to product features directly from their call summaries.
- Sentiment and summary automation: GenAI unlocks the ability to extract buyer sentiment on specific points from a discussion. It can also help generate personalized follow-up emails and improve productivity.
- Streamlined sales enablement: Sales teams can now take a multi-page sales enablement document and condense it into concise, email-friendly bullets or summaries, making information sharing more efficient.
GenAI, with its basis in language processing, effectively fits into the sales industry, which depends significantly on communication. It is capable of managing unstructured language data, including customer follow-ups and internal communications, making it a great fit for sales.
Managing realistic expectations of AI in 2024
Shruti broke down the top-of-mind challenges for the upcoming year into two aspects: from a technology lens and a business lens.
On the tech side, she explained that the biggest challenge would be in managing expectations both internally and with customers on what AI can realistically do for us. Right now, due to social media hype and the tendency of sellers to oversell the capabilities of AI in the hopes that technology will quickly catch up, everyone has sky-high expectations of AI. Naturally, this means that even if AI does manage to improve on the current situation, we will be disappointed as it hasn't managed to match our high standards. This leads us to develop a negative, almost dismissive attitude towards the effectiveness of AI.
On the business side, Shruti admits to keeping a close eye on the current state of the stock markets. While it's been interesting to see the stock market perk up a bit, the bigger economic picture hasn't quite caught up, leaving us to wonder if this upward trend will last and whether we ought to expect a bump down the road. It's a big question on everyone's mind, especially when considering business growth, inflation, and more. While tech companies often grab the spotlight, it's important to remember the vast, impactful world of other industries that, though less in the limelight, fundamentally shape our economy. This broader picture will influence how sales teams plan their targets for the year.
Taking an agile approach to planning for uncertain times
For 2024, Shruti and her team are adopting a 'let's take it as it comes' attitude towards planning their targets. Instead of setting everything in stone from the get-go, they are planning for the first half of the year with the intention to regroup and reassess for the second half. It's all about staying flexible and adapting to changes as they happen. This will give them room to breathe and adjust to reality, ensuring they're always moving forward, not just reacting to the world around them.
Shruti has also been encouraging her team to be more experimental with technology tools in the year ahead. Her advice to salespeople is to go out and be more explorative and open to technology tools. Rather than one person on the team evaluating five tools at a time, she's advocating a more collective learning approach. For a long time, technology was always something that was imposed on salespeople, but now they're learning that it can actually be something that's making them smarter, and making their jobs easier. Shruti believes that this year will be crucial in this shift in perspective on sales technology.
Want to learn more about Shruti’s thought process? You can watch it.
