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About This Episode
So… which comes first, the sales process or the sales technology?
It can be hard enough to implement new technology, but it’s harder still when that impacts your sales process — or requires you to rewrite it from the ground up.
I got to interview Jordan Greaser, Founder and CEO of Greaser Consulting, about how to avoid the frustration that comes with launching new sales tech.
Jordan is an Outreach alum who ran the whole sales development motion at Outreach when it was about $1M in revenue. “About a year and a half ago now I realized I could do some consulting,” Jordan said. Since then, he’s been having a blast with other former Outreachers exploring how sales processes and sales technology mix.
How to blend sales process with technology
Should your process inform what technology you use or should the technology inform your process? Chicken… or egg?
Most people start with their current process and add technology to it. That’ll get them some return on investment, sure.
“To me, both of those things have to come into play at once,” Jordan said. “What could our process be with this new technology and how does that need to change as we think about bringing this on board?”
The answer to whether process or technology should come first is both.
When you think about adding new technology, don’t just reach for what’s trendy. “When this new technology comes in, is the business impact enough that we need to reconsider what’s been constructed in the past?” Jordan asked.
The fact is that part of the process will probably need to change as you think about your whole ecosystem here. In other words, you can’t just take your current process, pull some technology in, and have instant and complete success.
Implementation mistakes
#1 — The do nothing mindset
It’s hard to get people to change their mindset from doing nothing to making a purchase. That change is the same when implementing a new tool or a new strategy.
“Folks are going through their own change management in their minds of what needs to happen, and they’ll just throw the implementation on somebody or the tool on somebody and say, go for it,” Jordan said, which results in frustration all around.
#2 — Execs only in the strategy session
Who needs to be in the room when a new tool or strategy is being decided? “Even in the cell cycle of deciding to bring something on, your frontline managers are key here because they’re going to bridge the gap between why you bought this and their team,” Jordan said.
Without the frontline manager involved in the adoption, everyone else will be clueless as to why this new thing is happening.
#3 — No empathy
Sellers can be resistant to change because their paycheck is aligned with how they’re working right now. If you change their methods, you could be impacting their income.
“The first thing you have to do is empathize,” Jordan said. “What is the reason why we’re making this change and how is it going to positively impact the seller?”
This is internal propaganda, but in a good way.
#4 — No enablement
You have to enable success. This might look like putting trainers into a class and explaining how to do this new thing. They’ll also need resources and longer term check-ins in order to stay accountable.
“We need all of those things to be firing to really affect change in an organization,” Jordan said.
Bonus: Provide a forum for publicly celebrating your reps’ wins and whenever your reps give you feedback, take it seriously.
Rapid-fire Q&A
Q: What’s your number one piece of sales engagement advice for individual contributors?
A: “When new tech knowledge comes in to your org, it’s not like everything is going to be perfect. It’s worthwhile in the beginning to just have fun exploring what this thing is.”
Q: What’s the number one piece of sales engagement advice that you have for the modern leader?
A: “Care about your people. What actually works is an environment where people care about them and are truly invested in their success.”
Q: What 3 things do you want people to remember from this conversation?
- Set expectations appropriately. If you’re going to hold people accountable for something, you have to tell them what your expectations are.
- Equip your frontline managers. After all, they’re the ones who are executing on what your goals are.
- Be flexible in thinking about how a new technology actually impacts the way you approach process.
Reach out to Jordan on LinkedIn to continue the conversation about sales process and technology innovation.
For more engaging sales conversations, you can subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast
The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.
Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.
The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.
Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.