Closing Time

The Sales-to-Marketing Career Change: Why Ex-Salespeople Make Great Marketers

People used to believe that marketing was an art and sales was a science, but today’s professionals know both require a little art and science to get the job done.

Whether you’re a salesperson interested in transitioning into a marketing role or a marketer who would like to better align with your sales counterparts, this episode is for you.

As a former SDR who now leads a marketing team, Kyle Coleman of Clari has first-hand experience in making the sales-to-marketing career change and advice for marketers to better collaborate with sales teams. 

By making small changes and adjustments – such as listening to sales calls, documenting processes, and prioritizing project management – marketers can begin to slowly bridge the gap between these two departments. It’s time to get both the right and left brains working together; you’ll be a ‘whole brain’ marketer with these tips.

Watch the video:
Key Moments:
Kyle's Career Transition from Sales to Marketing

Does working in sales make you a better marketer? How are those skills transferrable? Let’s take Kyle Coleman’s transition as an example. He started in sales development as the first SDR at Looker, a Business Intelligence Company in California. Over six years, he grew the SDR team from scratch to 70-strong. During this time, he shifted positions within the company, initially reporting to the CMO for four years and then to the CRO for the final two.

This trajectory gave Kyle a valuable perspective on both sides of the spectrum – his time with the CMO allowed him to become fluent in the language of marketers and understand their priorities, success metrics, and how the SDR function can support their efforts. Then, as a frontline salesperson reporting to the CRO, he lived through the discussions, processes, and concerns of salespeople – understanding first-hand how they can influence and support marketing efforts. He gained a holistic understanding of the entire go-to-market strategy as a result. When each function in the team is interdependent; there’s no need for clashes between marketing and sales. The goal is unity, with all team members working collaboratively to achieve the common objective: driving revenue and ultimately guiding the company to reach its goals and potential.

Tips to Help Marketers Better Understand Sales

It is impossible to be a great marketer without understanding who you are marketing to and why you are marketing to them. Sure, you can meet with the sales team and read enablement material, but the real magic is hearing directly from the source – your customers. Listening to recorded sales calls is like getting a sneak peek into the conversations between the leads you’ve worked so hard to prepare and your sales team. Using recording tools like Clari allows marketers to learn about customers’ challenges, what matters to them, and how they respond to your marketing language and materials. Here are a few other benefits of listening in to these conversations:

Direct Customer Insights: Listening to recorded sales calls provides a direct line to understanding customer challenges, pain points, and reactions to value propositions.

Authentic Language: By hearing customers talk, marketers can learn the words and phrases that resonate most with the audience, enabling them to create more relatable messaging.

Real-time Adaptation: Rapidly changing market dynamics demand quick adaptation. Insights from sales calls help marketers adjust strategies in real-time to stay relevant.

Collaborative Alignment: Listening to sales calls encourages collaboration between marketing and sales teams, fostering a unified approach that better serves customer needs.

Customer-Centric Approach: Marketers gain a deeper appreciation for customer concerns, allowing them to tailor strategies and content to address them.

Continuous Improvement: Regularly engaging with sales calls enables marketers to gather ongoing feedback and refine their tactics for more effective results.

There are no shortcuts here – marketers need to carve out time to listen to calls, talk to sales reps, and be open to feedback. The more time you can spend with your sellers and the more time you can spend with your customers, the better off you’re going to be.

Why Marketers Should Ditch the Jargon, and Adopt Simplicity

In a world where attention spans are short and competition is fierce, the ability to convey your message clearly and concisely is an underrated skill. Have you ever come across phrases like “360-degree view” and wondered what they really mean? You’re not alone – they’re on 9/10 B2B SaaS product pages. Jargon might sound impressive, but it often leaves your audience confused and your message diminished. Instead of opting for complex terms, aim for simplicity. Why not just say “full view” or “complete view” instead? This goes Long-winded sentences, intricate vocabulary, and fancy phrases won’t earn you brownie points. What truly resonates are concise, simple statements that get your point across effectively.

Kyle coins the intersection of Simplicity and Differentiation as the “sweet spot” of impactful marketing language. Where these two qualities intersect, success thrives. Trimming words and reducing complexity is much harder than it sounds. Getting your point across in just 10 words is significantly more challenging than writing a 100-word essay. That’s why Kyle recommends that every marketer read David Ogily’s books, specifically “Ogilvy on Advertising.” According to Ogilvy, simplicity isn’t just a preference; it’s a necessity. He believes that simple writing is powerful writing and that complex jargon and convoluted sentences only serve to confuse or alienate your audience. Incorporating lessons (see photo above) from David Ogilvy into your writing approach can lead to more impactful and compelling marketing communication.

The Power of Documentation and Processes

The influence of processes and documentation from your sales background can be a game-changer in your marketing role. As Kyle scaled his SDR team to 70 people, he realized that as a team leader, you are unscalable. You cannot expect every team member to absorb your knowledge – this is where documenting processes can help. 

The best sales and marketing leads will distill what’s in their head on paper. It doesn’t have to be a 10-page paper; a concise checklist will work wonders. Take producing a blog post, for instance. Who drafts it, who edits, designs, and publishes it? Frame these steps in an eight-point checklist so when your team members go to replicate it, they don’t have to wing it or invent their own process.

As a team scales, people will become frustrated when they are blindsided by tasks – which will inevitably disrupt their workflows. Creating processes creates predictability. And if you have predictability, your team is going to have a lot more unity and harmony. From a marketing standpoint, it’s a lot easier for the rest of the organization to know what is coming off the truck, what are the things that the marketing team is going to produce, and when. This product roadmap, but for marketing campaigns and content. The more visibility and predictability, the more equipped your sales team will be to support those campaigns. Embracing process and documentation isn’t about stifling creativity, it’s about ensuing that what’s planned gets delivered – a win-win for both the sales and marketing departments. 

How Marketers Can Lead by Example

Project management tools empower marketing teams to work more efficiently, communicate clearly, and maintain organized processes. If you’ve ever worked on a marketing team without a PM tool, you know just how important they are. But when it comes to introducing these tools and instilling a structure and process for project management, gaining buy-in from your team can be challenging. Kyle’s advice: leaders need to embody the mindset you expect from your team. If you want structure and process, you need to live it. Dive into the project management tool yourself, whether it’s Asana, Shortcut, Google Sheets, or even a simple checklist. By actively participating and showing your commitment to improvement, you set the tone for the rest of the org. Your dedication as a leader matters significantly. If your team observes that you’re not invested, it’s unlikely anyone else will value the project management system you’re trying to implement.


Can being a salesperson in a past role make you a better marketer?
Let’s talk about it in this episode of Closing Time.
Thanks for tuning into Closing Time the show for Go to Market Leaders.
I’m Val Riley, head of content and digital marketing at Insightly CRM.
Today I’m joined by Kyle Coleman.
He is the senior vice president of marketing at Clari.
And Clari is a revenue platform that improves visibility of team performance.
Kyle, welcome to the show.
Hey, Val, it is great to be here.
All right.
So there is a debate in my mind whether you came from the dark side
or you moved to the dark side, but you did shift from sales to marketing.
Can you talk about how that went in your career?
Yeah, it’s an open question and you’ll get a different response
based on who you’re talking to.
Are you talking to a salesperson?. Are you talking to a marketing person?
I’m a little bit of both.
I grew up through sales development.
I was the sixth employee at a company called Looker,
Business Intelligence Company based in California, and I was the first SDR.
I grew that SDR team to about 70 people over the course of six years.
But for the first four years, I reported directly to the CMO and for the final
two years at the company,. I reported directly to the CRO.
So I developed this, I think pretty interesting fluency of language
for both what matters to marketing people, how do they think about their work?
What are their success criteria?
How can I help them in this SDR role?
And then very similarly with salespeople, what do they talk about?
What do they care about, and how can the SDR role influence them?
And so I got this really interesting balance of the whole go to market team
and honestly each function can’t exist without each other.
And so it shouldn’t be this butting of heads.
It really needs to be a unified go to market team.
And it doesn’t really,
I don’t think about myself as being on one side or the other.
I think about being on Clari’s side, which is, you know,
this unified team of go to market experts that are all working in service
of the same goal, which is to generate enough revenue to hopefully at some point
become a profitable company and a company that can IPO.
And that’s the journey that we’re on together.
So, you know, as a marketer, and I’ve always sat on the marketing side,
which, you know, maybe. I should have switched team in the past.
But one thing that I do that
I am so intrigued by is actually listening to sales calls.
So like we have a platform that lets us as marketers
or anybody really listen to recordings and kind of hear
what the conversation is between this prospect,
that we have teed up as a marketing team.
And we have gotten them through all these stages
and they’re finally on that call.
And that’s such a powerful tool, right?
That’s just one tactic, though.
What other tactics do you think of that marketers can do
to really better understand what is going on on the sales team?
It’s a great point, Val.
And listening to those recorded calls is such a powerful weapon
for marketing teams that most people just don’t take the time to do,
which is a real shame.
A lot of marketers will do a lot of, you know, persona research
and they’ll look, read articles on whatever website, blog posts, whatever,
but they don’t actually listen or spend, get to spend enough time
speaking with the actual personas that you’re selling to.
And that’s what these call recordings can allow you to do.
I’d be remiss if I didn’t mention that Clari’s platform allows
has the capability of call recording, but will paper over that real quick.
The power of this is you get to hear directly
from the personas mouth you get to hear what are their main challenges,
what are their main pain points,. How are they responding to the value props
that the marketing team creates and the salespeople pitch
and the rapid iteration that you can make as a result of this is incredible.
So there’s no shortcuts here.
You have to take the time to actually listen to the calls, engage
with the field, talk to the sales reps, be willing to take some negative
and let’s say, constructive feedback about the types of things that are working
and what aren’t.
And especially in this environment,. Val, that’s changing
so rapidly, you’ve got to be able to pivot.
If you don’t pivot, if you as a marketer
get married to the messaging, positioning, whatever it is that you created a year
ago, two years ago, five years ago, that is a death sentence, especially now.
And so there’s no better way to keep or to iterate quickly and effectively
than to keep an ear to the ground and work closely with the field.
Listen to those recorded calls, spend time with customers.
If you could do those things,
you’re going to be much better off, you’re going to use language
that actually resonates,
you’re going to get out of your marketing ivory tower and down to the street level
so that you can actually create messaging that has real resonance
and you’re going to be a much better marketer as a result.
So that sales call is kind of like the bottom of the funnel.
But I was recently at a trade show
where I was shoulder to shoulder with some sales folks
and like we’re at the top of the funnel, but it’s the same experience.
You’re still hearing those conversations
like you’re saying, you’re out in the field
talking to real life people and kind of seeing as a marketer,
Hey, are the messages that I’m saying are the phrases that I’m putting out there,
are they really resonating?
So I would think that would be another great tactic to.
The more time you can spend with your sellers, the more time
you can spend with your customers, the better off you’re going to be. Hmm.
You know,
one thing that you had mentioned about helping sales and marketing teams
align, which we’re very aligned today because we’re like almost wearing
the same color but
is moving away from, like, jargon.
And in marketing and communications, keeping our messages shorter.
I mean, you had a bunch of tips in that regard that you feel that
sales folks see marketing folks maybe making these mistakes over and over again.
Can you talk me through those?
The jargon thing, Val, is so brutal and
there is nothing surer to
lose interest than using meaningless words.
How many times have you seen the phrase 360 degree view?
And you’re like, What?. What does that mean?
What could that possibly mean?
And yet, because it sounds fancy, basically you’ll see it on nine out of ten
SaaS B2B websites and it’s phrases
like that, like, what are we actually trying to say here?
We’re trying to say, you get a full view of something.
Why not just say that? Keep it simple.
And there are a million other examples of how that marketing jargon can
kind of infiltrate a lot of really strong value props and actually cheapen them
by trying to sound different, by trying to sound fancy.
You end up actually sounding the same as everybody else out there, and you lose
meaning by changing the meaning
in many respects of what you’re actually trying to say.
So marketers and this is part of what I love about having grown up
through sales development and growing up through outbound marketing is
you cannot afford as an outbound seller to use any of that jargon.
You need to speak simply, clearly and effectively.
And pulling all that jargon out is the only way
that I’ve seen successful cold prospecting actually work.
And the same is true with marketing.
The easier it is to understand, the more effective it’s going to be.
You do not get points
for using fancy words, for using longer words, for writing longer sentences.
That’s not the way that this works.
Crisp, simple sentences is what you want to do.
And if you can and this is hard.
This is the hardest thing about marketing.
If you can find the intersection between simplicity and differentiation,
when that overlap of that Venn diagram is the key to the castle.
Simplicity and differentiation.
If you can really nail
that, you’re going to be in much better shape than 99% of marketers out there.
I do.
I feel like sometimes I’m the hatchet woman when it comes to writing.
Like on all the teams I’ve worked on, I just want to come back and say,
No one cares.
This is too long.
Take out some words and marketers they tend to approach things
like they’re writing and it’s very personal to them and just teaching them,
the messages that you’re trying to communicate, you know,
just have to be shorter, fewer words,
more straightforward, less complexity.
Once they start getting that skill,. I know it’s one that’s going to serve them
like super long into their career, but it can hurt a little bit at the beginning.
It sure can.
And a lot of folks will say, you know, if it’s a simple sentence,
anybody could write it.
And that’s not true.
Simple stuff is harder to write.
It is harder to write a sentence that’s ten words than an essay that’s 100
if you’re trying to make one crisp point about your product.
And so paring it down and being really critical
about the exact verbiage that you’re using while you maintain that simplicity
and differentiation, that’s a really hard task.
I highly recommend for marketers out there.
If you haven’t been a student of David. Ogilvy,
go read everything the man has ever written.
He had a couple of books out there.
Ogilvy on Advertising is incredible, and you’ll see not just his principles,
but you’ll see his actual, there’s a lot of examples of the copy
that he or his agency has written over the years,
and it’s revelatory in how simple it is.
You don’t see any fanciness, you don’t see any jargon.
And yeah, this was happening 60s, 70s, 80s, whatever.
But human nature hasn’t changed that much.
Like people want to be able to easily understand something
and make a quick decision and the harder you make it for them to understand
something, the easier you’re making it for them to forget about you.
So you have to be really careful about that.
So it’s a great point.
Val. And please, please go, Ogilvy will talk about it better than I ever can.
He’s a personal hero of mine, so go check his stuff out.
Let’s shift gears just a little bit, because one thing that, you know,
we often associate sales with a lot of processes and documentation
and in marketing, we tend to think, oh, we’re more artistic, we’re more
we need to remove these boundaries because we have to be creative.
But one thing you brought from your sales background
into your marketing role was processes and documentation.
So it sounds like it might be counterintuitive, but you say it’s not.
It’s so important.
And again, for any lessons learned by scaling an SDR team up
from myself to about 70 people, is that you, the leader of your team,
are infinitely unscaleable and you can’t expect the knowledge
that you have in your brain to make its way into the brain of
the second team member you hire, let alone the 10th team member that you hire.
And so you have to at some point
swallow the pill and get what’s in your head down on paper.
What is the most optimal way of doing something, of doing all of the things.
And it doesn’t have to be,
you know, this a thousand word dossier on how to write a blog post.
You just need to, the way that I have found
success is thinking about things through the lens of checklists,
what are all the key things that need to happen here and in what order?
And if I can just write an eight point checklist about how to produce a blog post
and who the right people are that create the first draft
and do the editing, do the design, do the publishing, you know, CMS, whatever
it is,
then you’re going to be in much better shape than if you just try and wing it
every single time,
or if you try and just allow somebody else to go through a different process.
What ends up happening as a team scales, is you end up frustrating one another
if people don’t know what’s coming down the pike,
if people don’t know
what’s going to be asked of them when they’re going to get frustrated
and things will surprise them and it’s going to disrupt their own workflows.
And so creating process creates predictability.
And if you have predictability, your team is going to have a lot more unity
and there’s going to be more harmony there as well.
And then the benefit of this
from a marketing standpoint is it’s a lot easier to know
for the rest of the organization what is coming off the truck,
what are the things that the marketing team is going to produce and when.
And you can have a lot, it’s just like a product roadmap.
If your product team doesn’t have a process,
you can kiss that roadmap goodbye. It’s meaningless.
And so the same is true for a marketing roadmap, quote unquote.
And you need to be able to commit to what are the things that we’re going
to make happen, campaigns, events, marquee pieces of content, whatever
it is, share that with the field and then deliver on those things.
You cannot do that without a process.
So start small and create these checklist processes
for all of the different projects and types of projects that you have.
You’re going to be in much better shape.
You know, a checklist just feels so friendly and approachable.
So I can’t imagine getting pushback from that.
But just to be clear, you’re not talking about squelching creativity, right?
And in some senses, if you have those processes
and you keep everything orderly, you almost free up
people’s minds for even more creativity, like that whole brain.
We want the left brain, we want the right brain.
We want the whole brain in marketing.
That’s really well said, Val.
There’s a quote from Jocko Willink.
He wrote Extreme ownership, and one of the titles of the chapters
of that book is Discipline Equals Freedom.
And you think about that, you’re like,. Wait, what?
Discipline equals freedom.
But it really is true.
If people don’t have to think about the basic stuff, about how
things are going to get done, you can remove that all that anxiety
from their brain.
So that they’re unlocked to be creative within the process.
So there are guardrails,
but within those guardrails there’s plenty of room for autonomy.
There’s plenty of room for freedom, plenty of room for creativity.
And so that’s the structure that you want to create.
We know the hallmarks of what good looks like, and we know
the milestones that need to happen to get this thing across the line.
But we also know that marketing is a creative skill.
Writing is a creative skill, design, branding.
All these things require, right brain thinkers.
And so you have to be able
to find the right balance, find the right combination of both.
And if you can do that, you’re again
going to have that predictability for what’s coming off the truck
and you’re
going to have really interesting and impactful actual marketing materials.
So, so twice in my career,. I have joined a team where there wasn’t
a project management tool,
joined a marketing team where there wasn’t a project management tool in place.
And like,. I almost had like a little panic attack
and was able to successfully introduce those tools, you know, twice.
And I was coming in at a leadership role.
So what advice do you have for a marketing leader
to kind of coach up their teams with structure and processes in mind?
It’s a great question, Val.
The advice I would have is like, this has got to be top down.
You have to embody the same mindset.
If you’re expecting structure, if you’re expecting process, you’ve got to live it.
You’ve got to be the one in the project management tool, whether it’s Asana
or or Google Sheets or just a checklist or whatever.
You got to be in there reviewing things, eating your own dog
food, as the saying goes, and showing people that you’re
as committed to these processes and improving these processes as they are.
And I’m guilty of this as well.
It’s so easy, Val, to lose sight of this.
You know, how is the scarf woven?
It’s easy to lose sight of that
when you as a leader are doing a million other things
and probably operating at a different altitude, maybe a longer
term, more strategic level, but you have to make time to actually
go in and show the team that you’re leading by example
and that this kind of process actually matters.
And celebrate the things when they go well and
expose the things when they don’t go well and commit to fixing things.
And if you can do that and show your team that you’re really in it, that’s
going to go a super long way and there’s no replacing it.
If your team sees that you’re not in it,
no one else is going to care
about the project management system that you’re trying to enforce.
So you’ve got to be there.. You’ve got to show up. That’s true.
Lead by example.
It’s not new advice, but it definitely rings true.
Kyle, thanks so much for joining us today.
I’d like to think you’re on the light side and you left the dark side, but
we’ll leave that for another discussion another day.
It’s been a pleasure, Val, thanks so much.
And thanks to all of you for tuning in today.
Remember, you want to subscribe to this channel, like this video.,
hit the button for notifications so you don’t miss an episode.
We’ll see you next week on Closing Time.

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