Welcome back to the From Vendorship → Partnership podcast, Season 2: Seller’s Journey!
This season, we’re talking to B2B sales leaders about their experience building winning processes, coaching & scaling teams, and partnering with customers.
Our guest this week is Nick Casale, Director of Sales at Sendoso!
Nick was an early sales hire at Talkdesk when his coworker, Kris Rudeegraap, began having success sending coffee gift cards to his customers and decided to start his own company. He talked Nick into joining him at Sendoso, and Nick became their first sales hire five years ago.
Since then, Nick’s seen Sendoso grow from a pre-seed company to raising their Series C round last year – and has seen himself grow from an AE to the Director of Sales. In this episode, he chats with Ross about how to start building your early sales process and the importance of knowledge transfer when your team begins scaling.
Listen to the episode here, and get the key takeaways from our conversation below.
🙅 What do most people get wrong about startup sales?
“Not iterating quickly enough,” says Nick. “And not being honest with yourself if something isn’t working.”
A lot of people get married to something that either worked for them in the past – a process, pricing model, talk track, etc. – or which worked at first, but might not anymore. But for early stage teams, constant iteration is a must.
Be honest with yourself about what’s working, both in your sales process and in your team’s culture as a whole. Figure out what you want to keep as you move into the next stage of growth, and what you want to leave behind.
🔁 What’s your advice for building a repeatable sales process and training new reps?
Listen to what your customers want
It might seem obvious, but when you’re still figuring out your sales process, let your customers have a say in how they want to buy from you.
“If you’re hearing the same things from customers over and over, let go of your preconceived notions of what you think you have to do in your sales process,” Nick says.
Balance autonomy with consistency
When you only have a few reps, you might not have much of a defined process yet. Everyone is (hopefully) following a similar path and story, but it’s probably not thoroughly defined.
The hard part is taking all the successful pieces of your existing, scattered process and documenting it for all your new reps to adhere to – and figuring out the balance between autonomy and consistency.
“Figure out how much wiggle room to leave in the process vs. how much you dictate what has to happen,” Nick says. “Every rep has their own superpower and you want to help them leverage that – but you also need to keep everyone on the same page.”
Give your reps frameworks to follow
One of the most challenging things to manage as you scale is knowledge transfer between your reps: synthesizing best practices and ensuring they’re being followed across the team.
Rather than overwhelming your reps with dozens of Gong calls or pages of content to absorb, or simply giving them a script, boil down as much of your process into frameworks as you can.
Break down your buying process into simpler steps and – most importantly – share the “why” behind it. Focus on your customer’s problems and how you can solve them. You can support these frameworks with a script or extra content, but focusing on the “why” behind it helps reps digest the process easier and start selling successfully faster.
⚡ Lightning Round: Nick’s Fast Sales Insights
- Common misconception about sales? That it’s all about the money.
- Favorite app/software as a sales leader? Scratchpad.
- Another sales team you admire? Salesforce.
- Helpful book/resource? Start with Why by Simon Sinek.
- Hardest part of scaling sales at an early stage startup? Knowledge transfer.
About Nick
Nick Casale is the Director of Sales at Sendoso, the leading Sending Platform. As the third employee and first sales hire, Nick helped build Sendoso's initial sales process before stepping into management to focus on scaling the sales organization. Nick is passionate about empowering sales reps to rise above digital noise and connect with prospects and customers on a human level. Prior to Sendoso, Nick was an early sales hire at Talkdesk.
