Positioning That Sales Actually Uses with Jennifer Sillars

Welcome back everyone and actually welcome to something new.

If you've been listening for a while, you notice a change.

What was previously marketing genius unpacked is now marketing pack leaders.

With reason, my consulting practice has officially been rebranded from bit of genius to Thunder

Wolf consulting.

And if Thunder Wolf is about helping AI grow stage companies move the pack, then this show

is about learning from the leaders who already are.

So welcome to marketing pack leaders, where we unpack how product marketing positioning

and go to market strategy drive revenue impact.

I'm your host, Josh Porter, founder of Thunder Wolf consulting, where I help AI scale-ups

turn complex products into clear differentiated stories that sales teams can actually execute.

And today's guest fits perfectly into that mission.

Today we're tackling one of the most important and most misunderstood topics of product

marketing.

And that is having positioning that actually gets used.

And to help us with that, I'm joined by Jennifer Silas.

Jennifer is a product marketing consultant and a go-to market strategist who helps B2B

tech companies turn complex features into buyer-centered value.

With over a decade of experience, including roles at ARM and as co-founder of Cosmic

Strategy, she specializes in positioning, messaging, and aligning go-to market execution

to revenue outcomes.

Jen brings senior level product marketing expertise to scale-ups, aiming to make their

value obvious and irresistible to customers.

Jen, welcome to the show.

Thanks for having me.

I'm so excited for the opportunity to geek out about positioning and go-to market

execution.

Absolutely.

Absolutely.

Well, let's start here.

How do you know when positioning is truly sales-ready versus just marketing-ready?

Yeah.

So I think for me, it's all about the buyer's mindset and thinking about what buyers

need every stage of their journey, right?

Well, I think as the marketers, what we tend to do really well is do that really difficult

piece of sparking interest in the first place, like getting eyes on us and getting people

to start to consider us as a solution, but I think, and for my experience as a buyer

as well, once you click that request to sales call, request a demo button, your head goes

into a slightly different place, and if everything gets a bit real, right, and you're

thinking, is this worth it?

Do I have the time to actually implement this thing?

Like, do I really understand what I'm buying?

Like all these objections start to come to mind immediately?

So I think tackling those pieces is really important, and I think traditional positioning

misses a lot of the times, a big piece of like, why is this approach better than alternatives?

Why does this suit me as a buyer better than the alternatives?

Does the value justify the pain of purchase?

Like, it's not easy to buy tech, like, at the same time, I had almost a million-pound

budget, and I was looking at these point solutions that would have solved like a really nice,

like, concrete pain for me, but, and it wasn't even that expensive, so there was no budget

blocker there, but I didn't end up buying them, because I couldn't be bothered doing

like the 90s stuff, and justifying all these pieces, so the pain of buying is real, and

also that piece of like, will this decision hold up internally?

Right.

Right.

Just these pieces that a lot of the time, we don't tackle all the tricky questions.

Yeah.

Yeah.

It's, it's, if something's marketing ready, then, yeah, you might have some good response

in the market from people wanting to find out more, but if it's not sales, if it's not

sales already, when you're actually having live conversations and the positioning doesn't

address those live concerns, then it's not fully baked out, so I think you're totally

right on that.

Having these conversations and they're not able to really have a consistent narrative

around how the product's positioned, especially go over coming to friction of buying something,

then, yeah, that can be an issue, and the else can get lost that way.

Right.

Yeah, so easily, because it's always easier not to buy than to buy.

Oh, yeah.

Yeah.

Yeah.

And that's a great point, has a great point, because people will naturally, you know,

fall to the default, just, it's not going to do anything, no decision.

So, and that's where I think a lot of, a lot of deals get stuck as just a no decision.

Yeah.

Yeah.

That's the model and budgets are tighter than ever too.

Absolutely.

Absolutely.

Well, I think that's, that's a really great way to kind of think about how positioning needs

to impact not just the marketing, but also sales as well.

What are the most common breakdowns between positioning strategy and frontline sales execution

in your experience?

Yeah.

And I think it continues from what I was saying, it's that we've not fully thought about

what the buyer needs to hear at that point.

So, a lot of the time, actually, a really simple problem, why things are not being picked

up is that it's what we've delivered to sales is just actually a bit too cringy for anyone

to stay at one.

So, like, what lands in a headline is it necessarily what lands on a conversation at

a point where that, that salesperson is really trying to build trust and rapport and making

like big, huge grand statements like that gets eyes and an ad, but it kills your trust

and momentum there in that relationship.

So, I think a lot of the time we don't do the work of translating it down into a one-to-one

engagement level that's needed, that ties directly into value as well, quite often the

values pitched just that wee bit too high, so we can make big statements by like, we're

leading the transformation in XYZ, do you want to be part of this transformation?

That sort of thing, no salesperson is going to say that and no buyer thinks of themselves

that way either.

Yes.

You need to be much more focused on that person in front of you.

That champion, what do they need to hear?

And like I said, too often we are leaving some of the hardest biggest decisions up to

chance and letting individual salespeople just have to make these things up for themselves

and we just end up with so much variability in this really case thing, which where we're

having these additional conversations with an interested buyer.

Yeah.

Yeah, and you bring up a good point about when it comes to distinguishing marketing from

sales, it's about the number of people you're trying to reach.

Sales is one-on-one, much more intimate, and then marketing is about scale, as you've

used mass kind of communications.

And so it can't be tricky because those are different scales, that's why they're different

functions.

But that's why it's all the more important to have that positioning from marketing in a coherent

way so that every salesperson is going to have the same message, the same positioning,

and are prepared to answer the questions in the same way because if customers are getting

different answers from different people, then that causes confusion and then that can

lose your deal.

So yeah, you're absolutely right.

Having the ability to understand the buyer from their perspective and then having a coherent

message across marketing and sales is really going to help a lot of that.

But also, you said about being able to translate and take what the customer needs, take what

the company has, and try to bring that together.

It's like marketing, you have to be an interpreter.

You have to kind of, you're speaking the company's language, but you also have to speak the

customer's language.

Yeah, yeah.

And I think we are actually good at that and let's think about what positioning is in

the first place.

It's a strategy for influencing a certain group of people to think about you in a certain

way, where the world's focus and really what it should be is about why you deserve to win

that deal, why you deserve to win that market.

So the fundamental should carry through to the sales conversation and sales execution.

But it doesn't because, yeah, we're just missing some weak apps and bug and gaps are

prey.

Yeah, totally.

Totally.

Yeah.

Yeah, it's interesting because you have to be able to, you have to, with positioning,

manage perception.

That's really what it's about.

And I'm a big fan of the show Survivor and that's really what it comes down to to win

the game.

You have to manage perception.

You have all the, you know, these other players, you have to kind of filter through and yes,

you have to do good challenges.

Yes, you have to, uh, to be able to do well around the camp.

But in the end, it's about perception management.

And so it's very, very much what you're saying here is positioning in this core is about

perception.

How do people perceive you?

It's not about how you perceive yourself as a company.

It's about how your customers and prospects perceive you.

Yeah.

And I think that's why ICP and defining ICP as part of your positioning is so, so, so important

and getting to the detail of the ICP that actually makes a difference because I think it's

easy to lean back on, like, demographics and industry, a law, I think tech, loves an

industry niche.

Yes.

But there's, there's other things that actually are what you need to move on to more, like

buying trivers, like the actual pain, like actual jobs to be done as well.

I think the main job to be done back could be a bit because you're, if it's software,

right, but any sort of into me tech, they're literally using it as part of their job.

So you actually start to in already, like, there is a process there.

There's a task that needs to be done, they're, you're physically interacting with, like,

how they complete that task.

So I think that has to use so much more respect to it, rather than these, like, bigger pieces

like industry and, and demographics.

And it's funny because I feel like I've been doing this for like 10 years or something

now.

I don't know about you, but I never really spoke about ICP specifically for the last few

years.

Yeah.

For ever.

But ICP is cleverly, I feel is quite, is new earth.

Yeah.

Yeah.

It's interesting.

And I like to say, yeah, a lot of times people say ICB is ideal customer profile.

And sometimes I think that gets confused with a persona.

And I think about ICB is the ideal company profile.

So it's like, that's your specific account.

What's that particular company?

What's the revenue?

What's the series are they at?

How many employees do they have?

Those types of things.

And then you have to think about the key buyer persona.

And those, you know, those are your specific leads.

Those are the people you're going to be engaging with.

But yeah, I think you're right.

It's marketing 101 is understanding your audience and you can't understand your audience

unless you target that specific, understand in a target that ideal company profile.

Yeah.

And I think with B2B, like the ad in complexity as well.

And there's probably like some Venn diagram that I might end up doing on LinkedIn.

It's just come to mind.

But like ICP, for me, at least also includes your buying committee.

Mm-hmm.

Yeah.

Totally.

So that adds like this other like layer of weirdness in complexity to it.

Yeah.

When you, yes, you have to understand, like, and that's the whole thing about B2B versus B2C's.

B2C, you don't have to deal with one person, one decision maker.

But with B2B and it's in the company, there's going to be a, you know, group of, you know,

five to ten people making the decision on the CF to convince all of them.

However, as a marketer, you have to, you still have to target because if you're,

mm-hmm.

It's talking to multiple people.

You, you may lose the message for the most important person who's the ultimate decision maker.

And that decision maker may be because from somebody that, you know, the CEO tapped that,

like, says that they want them to be the, this specific initiative champion of, I need

like a new sales enablement platform or something of that nature.

Whoever is or a new HR tool and the chief HR officer or the head of HR is going to be in charge

of that.

They have to go, they have to have this committee of procurement, legal, finance and the like

to be able to go through.

And honestly, most of the time, that committee, the rest of those people besides the champion

are either the vetoing.

So that champion's going to be there to really self.

Yeah, yeah, because you're, you're kind of just like, I don't know any task to them.

Because they're not going to see the benefit of it.

And you can, you can kind of play to like the bigger benefits and obviously like roll

up to company-wide sort of stuff, but like ultimately as a one to one person, yeah, you're,

you're, you're just a task for them to do and they'd rather not have to buy something.

Um, yeah, it is, it is an interesting thing would be to be, I do like be to be this, this

level of complexity, like appeals, it's, it's, it's a sequencing issue as much as anything

and I think that similar with tech and how much you have to communicate to even the champion,

you have to make decisions about what comes first, like what's the value, what's going

to like pull them in.

And then similarly, then as you go through the sales process as well, you're feeding to

them the pieces of the value for their buying committee as well.

Yeah.

You have to think about like the whole journey through to do just it.

Yeah.

Yeah.

Yeah, exactly.

And I think that that model of working through buying committee, you ultimately have to,

you have to pick that champion and then that champion has to be the internal advocate to

all those other people on the committee.

And so you have to sell them first and then the others come, but you got to start, you

got to start with that, that, that primary decision maker.

That's my line.

Awesome.

All right.

So I want to move on to signals.

What signals tell you that adoption is happening and how do you course correct?

Yeah.

So there are a few signals.

So I think the most obvious one that marked your C and that we complained about most often

is that sales aren't using our materials, like they're not using our deck, they're not

using like even the one page or is they specifically requested, they're not going to need it.

Right.

Right.

You have no authorised.

Like they're doing their own thing.

I think that's a big indicator that you do have something missing that's, that's, they

feel is needed for the conversation.

Similarly, when they stop coming to you as the expert and asking like your opinion on

like the customer in the market, that's a huge warning signal for me.

Yeah.

The newbies when they're on boarding, if they're learning, you can see sometimes like a

really slow on boarding when they're just kind of drip, getting drip feds, understanding

of the customer by like talking to peers and like just having conversations within the

sales team themselves instead of having like this core understanding from the beginning.

Beyond those pieces, early funnel conversion rates is a big one as well, especially from

MQL through to ops, whatever kind of SAL you've got going on in your funnel.

But when there's like really big drop off from MQL into that level funnel, that's another

one.

The typical fights like leads aren't good enough from sales, same to marketing and then marketing

similarly through in sales back under the bus saying like, you can't sell to save your

life because sort of things.

Right.

Right.

So it's hard to open that and find something happens, especially when we're all against like

really high targets as well, like it's it's high pressure stuff that sales and marketing

piece like it's closer to revenue and more pressure, right?

Yes.

And that's where like fin fights about win loss and lack of clarity around win lost as

well, I think is another end of here because for me, that points back to you didn't know

why you should win in the first place.

You didn't know what your argument to win was.

Sure.

Yes.

And then also turn, like fast turn, like when you're winning like as soon as they possibly

can, then there's been a mismatch between what they wanted, what they were sold and

the reality of product.

Like I think those are very big painful signals that are actually all too common.

Yeah.

You're absolutely right.

You're absolutely right.

I think those are good to kind of think about if the first thing was going to be something

very internal up there, not coming to you, the sales teams that come to you for guidance

or direction on some of those, those sales pieces, the sales enablement pieces, then

yeah, that's, that's a problem.

You're there to be this connective tissue between product and the sales team and the customer,

honestly.

And sometimes some ways you should probably know the customer better than the sales team

who deals with them day in and day out.

So yeah, I think that's a good, that's definitely a good signal.

And then if they're just not using your content on top of that, then that shows that's a bit

of an issue and they're not, I like how you say, even if they've asked for a specific

one-pager and then they don't use it that can, it's like, that can, that can be a little

frustrating.

And so that could be for multiple reasons.

But you want to be able to give it, make it as easy as possible for them to have access

to it, but also that they understand it and that they're a continual reminder for that

it exists.

So that might be, you know, through multiple workshops or email reminders or whatever it

is that you are constantly on their radar.

And hopefully it goes back to the first one is they looked, they, you established a relationship

enough to where they come to you on a repeated basis.

So hopefully you've got that basis, but then they're also going to be some reminders that

they're really key, I think.

So.

Yeah.

So I think, I think you point about we should know the customer in the better than them.

I think that, that is really important because if nothing else, we are getting, or should

be getting, a broader perspective of the customer, so it's sales input, so valuable.

And we all wish that we could hear like every single sales call, right?

Because we would learn.

Yes.

But we're also, like, we also have the benefit, like we're talking to product, we're seeing

the literal reasons why these features are being created, like that's a level that they

don't have.

You're also doing your own research about like trends in the market and like buyers in general

and from customer success level as well, you're seeing like how people are actually using

the product, like what they're actually having problems with, like this is culmination

of all this constellation of points from different areas.

Like, I think that's where we, we hold value and that's what we should always be aiming

for.

And that's what will make them keep coming back to us and they feel like we do actually

have insight to offer that they don't have.

Yes.

Yeah.

And I like how you circulated that.

It's bringing some of the customer inside along with the product inside because you're

kind of, I had one way to cause product marketing, the great in between.

So you got to, you got to have some of the knowledge that comes from all those pieces

and be able to package it in a way.

So that the sales people can use it and the customers understand it.

And then I also like what you pointed out about sometimes sales isn't able to articulate

why they want something and that's, that can be an issue because you want to be able

to repeat that.

You want to be able to say, was it because we spoke about this particular feature, this

pain point or they like these parts of our offer and having an understanding of why you

win is as important as why you lose because if you want to repeat that, you need to have,

you need to have that written down somewhere, you need to have that as fodder for other

sales people.

Yeah, absolutely.

And I think sometimes we're, we're scared to be prescriptive with sales.

And I think we should be a bit braver at those earlier stages because we should definitely

allow sales to build a report on that account, get into like the nitty-gritty of what that

can cares about, but at those early stages and like say like the first proper sales conversation,

you don't have any of that yet.

So we should at that point, I think, be pretty set on the minimum, what I actually call

minimal viable buyer understanding.

So like the key points you have to hit that is your take permission of why they should

choose you.

Yeah.

It's your position strategy.

Yes.

Yeah.

Yeah, like I said that it's at the very beginning stages, you're not going to have all the information

you need to get super custom.

So you do need to have, you need to have a strong position at the beginning to kind of establish

that foundation.

And then you, that's, that's all point of the discovery call is to get more information.

But you need to come with something, you need to come with a point of view in order to

get, you know, get the conversation going.

Yeah.

Yeah.

And I take Scott's to like put a real line in the sand about this is the type of customer

that you're best for.

If you recognize yourself in this, we're the ones for you, it takes bravery and sometimes

probably that's where we're from that a little bit.

Yes.

Yeah.

Totally, totally.

Awesome.

Well, I think this has been super good to kind of see and understand a little bit more

about your expertise and trying to help bring positioning into end of the line sales tactics

that hopefully hit the customer and when customers over.

So with that, I'd like to go into our rapid fire round where I ask all of my guests the

same questions and love to hear the different responses.

And I think you'll have some, you know, good insights here too.

Are you ready for these rapid fire questions?

I'm ready.

Awesome.

All right.

Well, first off, what's your favorite marketing tool?

Um, Claude.

Oh, yeah.

Tell me more about that.

Wow.

And Claude could work now is all my my efficiency goals and hopes for this year onto Claude

could work.

Yes.

Awesome.

Yeah.

Definitely that there's new capabilities, definitely make it help automate a lot of things

for you, especially as a knowledge worker.

So that's, that's, that's awesome.

What is in your opinion, the most underrated skill and product marketing business acumen?

I think more, I think that engagement with, because I think positioning, strategy is

just your fundamental business strategy is why you exist in the world, why you deserve

to win.

It's the center of everything.

So from what I see, the PMM's that have done amazingly and who have that consistent

seats at the leadership table, they understand the level that they should be playing at.

And they have the engage with all the fundamentals of the business, at least have an interest

in like commercials and the product and all the pieces come together, because I do think

that positioning strategy is fundamental business strategy.

Yeah.

Yeah, you got to, you got to, you know, you need to say in your function for sure, but

you need to kind of go higher level now, you have to have that overall business, understanding

business acumen to kind of put the context together.

So yeah, I think that's great.

Absolutely.

What's the biggest mistake to avoid in product marketing?

I think waiting to be asked opinions, like we're saying to like, we should be amassing

that that wider view of the customer, we should be embodying that voice of the market

and just bring it in wherever, wherever we can, like we need to be, we need to lead.

Yes.

Yeah.

I remember there was a later said, don't wait for permission to lead, just lead.

And now also ties in with actually listen to this at a product marketing alliance summit

a few years ago, which is happening right now in New York, as a matter of fact, they

are basically saying how you just need to have an opinion, you need an assert an opinion.

It doesn't matter if you're wrong, like in the end, it doesn't really matter if you're

wrong, because at least you're showing you've got some point of view.

And so I think having that point of view that gives at least some people something to react

to, because then if you don't have something for people to react to, then in a way, you

kind of don't exist.

Oh, no, absolutely.

I love like a strong argument, like just to bring something to the table, it's the only

way to get things moving.

Especially when you're seeing your leaders, like the time is precious, when you want like

things to be moving forward, you need to lead.

Yes.

And one more thing I'll add to that, but I think it was interesting, or one boss told

me, he said, he's like, people may agree or disagree with your opinion, but when you

don't have an opinion, they don't respect you, they won't respect you with that.

So, you know, I think that's really key.

It's like some people are afraid of not being agreed with, but in a way, I'd rather be

disagreed with than ignored.

Oh, absolutely.

Yeah, and I think anyone who has been in those meetings with senior leaders, like it

fights an argument nonstop, like that is actually the norm, like everyone's expected

to be the voice for their function and put it on before us.

Absolutely.

Absolutely.

All right.

Next question is, what's one thing you wish you knew when you started?

Oh, that's a tricky one.

I wish I knew more about sales, actually, unlike the reality of the sales.

I don't think it was until I had to do it for myself this last year that I fully got

what the issues were.

So I would have been an amazingly more helpful marketer if I figured that I sooner.

Yeah, totally.

Yeah.

That makes sense.

Yeah, it's definitely something that we all have something that we're like, oh, after

a few years of experience, like, yes, we should have done that, but live and learn.

Live and learn.

Okay.

And last and most important question is, what's your favorite podcast?

Okay.

I get out into this one for about half an hour.

I love a podcast.

I think probably the one that I would want everyone who's listened to this, if they haven't

listened to already, the acquired podcast.

Okay.

So especially when they go through the stories of all the biggest companies in the world

and how they got to where they are and what was their moat and what was behind the scenes

of it.

And they've got a lot on the kind of, like, tech, like, historic tech companies that now

can be seen today, like, get more on the chipside and all that.

So it's always just so so interesting.

Beyond that, I love a true kind of, true kind of stuff, all of them, all of them.

I know we, like, funny ones, but like, last podcast on the left is like a dark humor.

Interesting.

Okay.

Okay.

Cool.

Well, those are some good ones.

I've heard a couple of clubs have acquired.

And then true crimes always interesting.

And then that last ones, I'll have to check that out too.

So those are good.

Those are good recommendations.

Like, you know, some that are business focused and some that we need, we have to have

to life outside of business.

So those are going to get the interest, be, be good to listen to.

All right.

Then, well, this was fantastic positioning only moves revenue.

And I really think that you have grounded it in its execution.

So thanks for explaining how you try to make positioning real for sales people.

And thanks for being on the show today.

What did I have in mind?

You bet.

And everyone else, thanks for listening.

This is marketing pack leaders, where we explore how modern product marketers and go to

market leaders build differentiation that actually converts.

You can find this episode on Apple podcasts, YouTube and Spotify.

I'm Josh Porter for Thunderwolf Consulting.

Thanks for listening and we'll see you next time.