Tactical Tips for Leadership, Strategy & Sales Execution w/ Sam Taylor

10/10 GTM Episode 1
Transparent sales process - working together
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Welcome to Season 1 of 10/10 GTM: The Podcast for Revenue Leaders.

This season, we talk to legendary leaders such as 5x CRO John McMahon and execs from 6Sense, JB Sales, Gong, and Chili Piper about how to drive consistent sales execution — leading to predictable forecasts (and better sleep). 

Our guest this week is Sam Taylor, CRO at Endgame. Sam’s background is predominantly in sales, with experience at Dropbox, Quip, Salesforce, and Loom. But outside of the office, he prioritizes getting outdoors and spending time with his family. 

In this episode,Ross talks to Sam about leadership, strategy, and execution within revenue orgs. 

Listen to the episode here, and get the key takeaways from our conversation below. 

The hardest part of going from managing a team to a whole department

The shift from managing a team to a full department naturally comes with this unique set of challenges, but at its core you need to be intentional in what you are doing and ensure communication is prioritized. 

Communication - People require effective communication to be seen, hard, supported, and ultimately to perform at their best. But dynamics change when you are managing a larger org, and you need to be far more intentional. From 1:1s to team syncs, and larger strategy meetings, strong communication is key.

Building relationships - Building relationships gets really hard when you’re in a massive organization, and it's important to find ways to prioritize this in a scalable way. For Sam, he would leverage Loom (when he was working at Loom), to do a Monday morning update of what he was up to over the weekend, how he spent time with his family, etc. You cannot necessarily manufacture those “coffee machine run-in” conversations, but this is a step that really helped. 

Various departments and goals - The biggest piece with a larger team is ensuring everyone knows where they fit into the broader strategy. Part of this is leveraging your team and ensuring that your functional leaders have an understanding of how the business is operating, but also empowering them to distill that information in a digestible way for the team. 

3 tactical tips for sales strategy and execution in a revenue org 

  1. Get to no quickly - Ensure everyone is using their time in an impactful way. If you’re pulling multiple people into the deal, make sure its valuable. 
  2. Activity auditing - Look at your champions and users in either a pre-sales cycle or proof of concept (POC) of some kind. Ensure you actually know what's taking place with those users - people speak with their actions, so even if they have a free trial, ensure they are using the product. All this information can help when you’re in a deal review so you can ensure you have tangible movement of the deal. 
  3. Executive alignment - Ensure you are bringing your SMEs and executives from across your company. Help put your leaders to work. Making sure you have a sponsor who feels some sort of ownership over the deal is huge.

What revenue leaders do wrong when it comes to driving consistency and predictability with deal execution 

Achieving consistently and predictability in deal execution is incredibly important, but it's also a place where leaders can fall short. Some of the areas leaders can fall short: 

Alignment - If your entire team doesn't understand what excellence looks like, and isn’t applying that to every deal you will feel it across your org. 

Rituals & clear expectations - Your team needs a consistent rubric that guides forecasting and deal reviews. This trickles down from leadership to frontline managers and their teams. Everyone must be on the same page and understand what is expected of them to be successful. 

Deal inspection cadence - Deal inspections can vary depending on the stage of the deal cycle. If you are not amping up your cadence of inspections as deals progress, you will likely fall short.  While you may kick off your inspections weekly, as you near the crucial phases, such as budget discussions and project qualification, increasing the frequency to bi-weekly is beneficial. In the final stages of execution, when you are closing in on signatures, daily updates become crucial, especially during end-of-month or end-of-quarter events.

Rapid fire: Sam’s fast sales insights

In a rapid-fire Q&A session with Sam, we discussed the key aspects of revenue leadership. Let's dive into some quick insights:

What's the main reason most teams miss their ARR goals? Truly qualified pipeline is not big enough. You need a big pipeline - that solves everything. 

Favorite resource related to revenue leadership? The 20VC podcast.

What's the number one challenge for revenue leaders in 2023? Target setting.

SMB, Mid-Market, or Enterprise? “You’re asking me which child is my favorite. Mid-Market.”

Most important org: new business sales, customer success, or marketing? A soft spot for sales, coming from a background in SDR corporate sales at Salesforce.

Best way to unplug from the demands of revenue leadership? Get outside, connect with open spaces, put away screens, and find grounding in nature.

The road to successful revenue leadership is paved with? Authenticity.

About Sam 

Sam Taylor has over a decade of sales experience, and kicked off his career within a Sales Development capacity at Salesforce. Eventually he took his talents to organizations such as Dropbox, Quip (acquired by Salesforce), Loom, and now Endgame.