Tiffany Regaudie is a marketing consultant and writer who specializes in brand positioning, content marketing, and empathetic copywriting.
Having worked several years in tech, Tiffany decided to carve her own path as a freelance marketing consultant who helps companies find their customers and get noticed with pitch-perfect copy.
In this episode, Tiffany and Mohammed talk about how Canadian freelancers can position their business to stand out from the noise.
Short on time? Skip to the parts you're most interested in.
[05:19] Getting started as a freelancer
[07:19] Helping clients set their positioning
[10:35] Understanding positioning
[12:57] Example of positioning
[18:09] Mistakes freelancers make with positioning
[20:43] Finding your niche and best-fit clients
[23:02] Positioning your freelance business
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Tiffany: I’m excited to do this. It seems like something really fun to be a part of, so thank you.
Mohammed: Yay! I’m super excited to talk about positioning today, mainly because I am big on positioning. I think once you figured out your positioning, that just has such a rippling effect on the rest of your business. A lot of times, I find people think that positioning is part of a marketing exercise when really it’s more of a business exercise and it should come much, much, much earlier as part of your larger strategy.
Yet not as many people understand it fully. So, I’m super excited to get into this but, before we get there, I think we should take the time to understand what is it that you do as a freelancer.
Tiffany: I’m Tiffany Regaudie and I am a marketing consultant and writer. So I specialize, as a freelancer, I specialize in advising early-stage startup founders on the foundations of their brand and that does include positioning. So, I love, as a consultant and as a freelancer, I love untangling complex ideas and I love doing that with founders, particularly founders who haven’t necessarily found their product-market fit yet. I love establishing the unique value proposition that their business is going to offer a target segment.
So identifying their audience and really helping them think through all of the possible angles of their business and then distilling all of those complex ideas into something that is easily understandable and forms the framework of their brand. So all of the foundational assets like their mission statement, really like the nitty-gritty beginning stuff that people take for granted when they walk into a company and that that company just has a brand, I like building that stuff from the ground up with writing in particular.
Mohammed: And given that you work with a lot of early-stage founders, do they have money?
Tiffany: Yeah, yeah. Some of them have money. That’s a great question. Yeah. And I definitely thought about that, in my own work, yes, I think that it varies. There are some founders that have more money than others and I’m going to go after the ones who have a little bit of money to spend, but, yeah, I charge reasonable prices, taking into consideration that, at that early stage, you’re probably — like you probably don’t even have seed funding yet and so you’re bootstrapping that yourself and so, yeah, my prices reflect that early-stage scrappy startup life.
I’m fascinated by the struggles that early-stage founders face particularly. They’re pretty unique and they’re pretty emotional.
Mohammed: Right. And what has that experience been like? I mean, or better yet, I think, what made you decide to focus on the early-stage founder market?
Tiffany: So I have experience — so because I have done it before and I know — I’m fascinated by the struggles that early-stage founders face particularly. They’re pretty unique and they’re pretty emotional, and so I kind of like the emotional entanglement that is involved with figuring out what your company is in that early stage.
I’ve been there before, I’ve walked founders through that process in an in-house capacity so I really understand the emotional nuances of having somebody take a magnifying glass and looking at your business from an objective point of view and really untangling the bits and like being real about like what’s going to get thrown away and what’s useful and what’s compelling. So, I’ve done that in-house and so I wanted to take that in-house experience and apply it to more of a freelance consulting environment.
Mohammed: Great. And what made you decide to start freelancing?
Tiffany: It’s something that’s been on my mind for a very long time. I love to travel. I love moving around. Even when I was in-house, I wouldn’t spend that much time at companies. I think the longest period of time that I’ve spent at a company is like, I don’t know, just under two years. I like variety. I really, really like variety and I like freedom. So, number one, I like working on projects that have a beginning, middle, and end. So, I don’t know, like way back when I started my career in book publishing actually, a long time ago.
What I love so much about book publishing is that when you make a book, there’s a clear creative process that has a beginning, middle, and end and then you get those books in a box from the printer and then you promote that book but it’s a contained project that has a clear goal and reaching that goal is super satisfying to me. And so I love project-based work and so like — I like my in-house work but it was just kind of like ongoing and without that kind of a wrap-up and the potential variety. I would kind of get bored a little bit.
I need a lot of variety, but then I also love freedom, like I love working on my schedule. Obviously, we can’t really travel right now but when travel becomes a thing again, hopefully, like, I don’t know, the next year or two, not gonna make any predictions about that, but I do want to explore digital nomadism because I do love to travel so, yeah, I would say like the clear project-based life and the freedom of my schedule. Every decision that I make in my life is working towards being as free as possible. So, yeah, that’s really why I went the freelance road.
Mohammed: And I find it interesting that you’re working with early-stage founders, helping them think through their branding, their voice and tone, their overall content, and I suppose positioning, right?
Tiffany: Yes, yeah.
Mohammed: So, how did all of that come about? How are you the person that maybe most people that are coming to your site might not realize that “Oh, you know — Tiff? Tiffany?
Tiffany: Tiff is good. Yeah.
Mohammed: “Tiff is a content writer and let’s bring her in,” but when they bring you in, you’re like, “Oh, actually, it seems like you don’t have your positioning figured out, let’s work on that.” So what happens there?
Tiffany: Yeah, you know what, you just reminded me of such a great conversation that I had with two kind of unofficial mentors that I have, Johnathan and Melissa Nightingale —
The best salespeople don’t necessarily try to sell you a product or service. They make you realize that you have additional pain points and that there are solutions that you may not have thought about.
Mohammed: Oh, yeah, I love them.
Tiffany: Yeah, I love them. They’re fantastic. When I started my own consulting business, they reached out to me. Johnathan reached out to me on LinkedIn and he was super — he said, “Congratulations! If you ever want some advice, we’re here to offer you advice,” and he was just so nice. He was so just generous with his time and I was like, “Yeah, I would love to take 30 minutes just to kind of pick your brain about something,” and Melissa and Johnathan, they told me that the best salespeople don’t necessarily try to sell you a product or service.
They make you realize that you have additional pain points and that there are solutions that you may not have thought about and so they kind of gave me an example and right now it’s funny. I’m talking about positioning but I’m still working out my positioning because I am a writer and so I do a lot of that kind of like bread and butter, like copywriting, SEO, blog writing, that’s a part of my package.
But Melissa and Johnathan, they were like, “Well, if somebody contacts you for writing work, you might want to consider really untangling their product or service and perhaps, if it’s warranted, if it’s applicable, make them understand there [are] positioning problems within their offering that you can also fix,” and so I really took that to heart and it’s always difficult telling a founder that they might want to tweak something about their fundamental offering.
Again, [as] I said being an early startup founder is a very emotional experience, you’ve created — and you know this, I mean, you’ve created something that’s like a child, you know what I mean? That’s like your baby and so, to have a consultant come in and say, “You know, the foundation of this might not be as solid as you think it might be but here’s the solution, here’s a possible solution,” it’s a very difficult thing to do but it’s also very satisfying when it can work.
Mohammed: Perhaps we can take a pause here and address what is positioning? Because not everyone will know what we’re talking about so maybe it’d be good to dive a little bit into that before we continue our conversation.
Tiffany: Yeah, that’s a great question. So, I kind of adhere to April Dunford’s definition of positioning. I read her book a couple [of] years ago I guess now, Obviously Awesome, and I thought it was one of the best marketing books I’ve ever read. And she defines positioning as kind of the act of identifying the unique value that your business offers to your ideal market segment.
And so you mentioned earlier that there are a lot of people that think product positioning is a marketing exercise and I also absolutely disagree with that because no amount of marketing spin is going to make a buying segment buy your product or service if they don’t need it and they don’t want it. So, positioning needs to be like a fundamental business exercise as to who your product serves and what is the unique value for those people. It’s really — it’s about — it is the process of finding product-market fit.
You might run through product positioning exercises like alongside interviews with customers when you’re trying to find product-market fit and I guess like to bring it back to freelancers, specifically in the freelancer context, you should be treating your service the same way so you should be treating your service as finding your product-market fit and, as a freelancer, positioning is about finding your niche and finding out who your ideal client is and what is your niche, what makes you special, what is your specific angle that no one else is offering?
So, yes, like the outcomes of figuring out product positioning might be marketing exercises, because you have to express your position but the root of it is not necessarily a marketing exercise, it’s a product-market fit, [an] entrepreneurial, foundational exercise that you do early on in your business and ongoing.
A tangible company example of a company that understands their position is actually Hinge, the dating app. Their tagline is “Designed to be deleted.”
Mohammed: I mean, I’m still working on an example that is tangible for everyone as to what I mean by positioning, but I’d love to know if you have an example that you usually turn to to [explain] what positioning is.
Tiffany: Well, I have a really good example and I use this frequently, like a tangible company example of a company that understands their position is actually Hinge, the dating app. Hinge — yeah, you might want to check out their website and just kind of their general marketing, but their tagline is “Designed to be deleted,” and I just think that that is so — it’s so telling to me about their position in the dating app market because I could totally picture like “Designed to be deleted,” that outcome is obviously from a positioning exercise that they did, specifically positioning themselves against Tinder.
Because if you think about what Tinder — and positioning like it’s not just about identifying your ideal customer, which in this case, for Hinge, they obviously want to target people who want to find meaningful connections and deep relationships, but that pairs well with positioning themselves against Tinder because Tinder has this reputation for being a hookup app. And so Hinge kind of took a look at that and said like, “Okay, well, Tinder is where you go to like hook up with somebody, but Hinge is where you go to actually find a meaningful connection and eventually, the outcome is to delete the app.”
So I just think that that’s such a strong example of an outcome of good positioning just because it’s holistic and positioning is holistic because you’re considering who your ideal target customer is, you’re considering what are all of the other factors in the market that are going to influence somebody choosing your product.
Mohammed: I’m on — I pulled up Hinge’s website. So, yeah, “the dating app designed to be deleted.”
Mohammed: I like that. It’s very much to your point about if you have if you build a meaningful relationship, may not need the app at all, where if I go into Tinder’s website, it says “Match, chat, date,” there’s nothing about deleting or like what happens forever after. So, to your point exactly that it’s more of a dating or a hookup rather than building a meaningful relationship.
Tiffany: Yeah, exactly, which is essentially the ultimate benefit of the product, right? And I mean, that’s — yeah, positioning is really — it’s the exercise of untangling what you’re offering so that you can get to the ultimate benefit and then marketing is just expressing that benefit in all sorts of creative ways.
Mohammed: I think the value prop on your website is quite nice as well too, which is “Freelance copywriting you’ll barely need to edit” which I thought was very — at least coming from my experience working with some freelancers in the past how can I trust them enough to go through and edit it?
It’s just like — it’s like that’s not the solution, [as] my thought process like when I was hiring someone was like, “Hey, I’m hiring this expert and I don’t have to think — I’ll never have to like think more about it,” but it always ended up being like, “No, I actually have to do more work than I was expecting,” and perhaps that’s part of me on project scoping and it’s another part too like work with someone who’s still sort of figuring out their freelance business.
So, the fact that you say, “Hey, freelance copywriting you barely need to edit,” to me, that’s just like, okay, that’s a value proposition and I am a target customer because I don’t want to edit the work that I’m paying for or working with a freelancer in the early stages.
Tiffany: Oh, yeah, and that it’s so funny, I — that value prop came very easily to me because I used to be that person too, right? I mean, I worked in-house, I was the content marketing manager and, yes, it was such a common problem where I would hire a freelance writer, they’re supposed to make your job a lot easier and then I would end up just getting back to work and practically rewriting the piece when it’s supposed to save you time, right?
You hire a freelance writer so that they can write articles for you and then it’s reasonable that you would have to do a copy edit and check for brand voice and things like that. There are, of course, reasonable edits that have to be made to any article when you get it back, but a constant problem was having to rewrite the article to the point where I was like, “Why did I hire this person? I could have just written — like I could have just written this myself and still saved time.”
So, yeah, I used to be the audience that I am communicating that value prop to so, yeah, that one was almost a no-brainer for me.
I think a common mistake is that freelancers try to be everything to everyone and, more specifically, they don’t spend enough time identifying their ideal client.
Mohammed: As we dive a little bit deeper into positioning and even like looking at different websites that there are, what have been some I suppose blunders or mistakes freelancers that you’ve talked to made or have experienced themselves when positioning their business?
Tiffany: Yeah that’s a really interesting question. I’ve been thinking about that a lot because I am in the beginning stages of my own business and I think a common mistake is that freelancers try to be everything to everyone and, more specifically, they don’t spend enough time identifying their ideal client and I recognize why and it’s because, in the beginning especially, you just want anybody to pay you, like you’re just like, “Oh, my God, I’m on my own,” there’s a lot of fear, right?
Like, I mean, it’s all emotionally driven. There’s a lot of fear of going out on your own, especially depending on how much financial cushion you have. So, there’s a lot of socioeconomic privilege kind of baked into these beginning stages of being a freelancer and you’re just kind of out there and you’re like, “Okay, I just need to find somebody who will pay me as quickly as possible to do work so that you can start to get word of mouth and you can start to like build your client base.”
So because they’re driven kind of like by that fear, they don’t spend the time identifying their ideal client and who they really want to work for and what kinds of projects they want to work on —
Tiffany: — which can be a mistake because those early clients that you get, they’re going to be the ones to be your early referrers. So like, ideal situation, you do a really good job, they start raving about you to everybody that they know. That’s the outcome that you want, and if you end up working with people whom you don’t want to work with those kinds — that that target segment long term, well, you’ve just started kind of a snowball effect and you might keep getting clients that you don’t necessarily jive with.
So, I find that’s the biggest mistake. But it’s tough because it is tied up in a lot of fear about money and things like that. So, it’s a very understandable decision or mistake to make, but I do think that saying no to some projects for clients that you don’t necessarily want to work with could help in the long run.
Mohammed: And even to the, I would say what type of customer you want, I guess I think I’m trying to understand is there will always be people that would say, “Hey, this is my ideal customer,” when perhaps, in reality, that actually might not be the ideal customer for the type of services and products they provide.
What has been your experience with people who need to, I guess, shift their mindsets as to how to go about finding the right client and determining how their skill sets align with a client that may not be who they think they are?
Tiffany: Yeah it’s interesting. I think that kind of just goes back to having to find your niche which is very analogous to finding [a] product-market fit in an in-house startup environment, right? And one of the pieces of advice that I would give to freelancers is like the process of finding your niche is the process of validating a product and so I am a writer, I’ve been a writer for many, many years, and my advice would be to start generating creative assets that speak to what your niche is and speak to your ideal target client.
So, start a blog, start a newsletter, just start writing posts on LinkedIn, start tweeting more, and once you kind of put creative assets out there, even if they’re not perfect and they don’t speak to a niche that you are sure that you want to commit to, it gives you information and I think like that’s — and this is like somebody who’s starting a business, it’s the same idea with product validation, you release something, you put out a survey, you interview customers, you kind of have to treat it the same way when you’re a freelancer but like in a little bit of a different — using different methods.
Like writing a blog, seeing how people respond. Did people respond favourably? Did that post not get as much traction as you thought it would? And what niche does that content speak to? That will kind of help guide you in finding your ideal target client, but you just kind of have to put stuff out in the world and see what you get back and that will be your compass is kind of what I say.
Who are the freelancers who are offering the services that you’re offering, but what are the behaviours that your ideal client would engage in if they don’t hire you?
Mohammed: Right. And so for those freelancers that are perhaps getting started or looking to rethink their business, how can they get started on ensuring that they’re positioning their business better?
Tiffany: Yeah. So like, I, again, like I ran myself through April Dunford’s positioning exercise and she does things in a very interesting order that I really, really like. So, that’s just kind of like imagining your ideal client. It’s kind of like what are the characteristics of the ideal person that you want to work with? So like always start with your audience, that’s kind of a Marketing 101 anyway, but imagine your ideal client.
Then the second step, which I also really, really appreciate, is [to] imagine your competitors, but April Dunford, she identifies competitors as also behaviours and so it’s not just like who are your competitors, so like who are the freelancers who are offering the services that you’re offering, but what are the behaviours that your ideal client would engage in if they don’t hire you? And so that could be [to] do it themselves, right?
Like that’s a — a competitor is the client themselves sometimes, especially in an early-stage startup environment where there is kind of like a lack of money, but competitors too is the client trying to figure out positioning and marketing and communication by themselves and so you have to take that into consideration when you’re drawing up your benefits, which is the next step.
So take the ideal characteristics of your client, take the competitors including the behaviours that they would engage in if they do not hire you, and that’s kind of when you come up with the features and benefits of your product offering and I would say like when you’re engaging in a positioning exercise, as a freelancer, let steps one and two really dictate the outcomes of the features, so your services, and then following that, the benefits of your offering.
Do that kind of like deep-dive work. A lot of people are just like, “Well, I like doing this, so that’s what I’m gonna offer,” and it’s like, okay, of course, like you have to find personal joy in what you’re doing but let steps one and two refine and guide your offering and you’ll see your services through a new lens if you take the time to engage in those first two steps.
Mohammed: Right. So somebody could come in or maybe getting started and it’s like, “Hey, I want to be a B2B SaaS copywriter,” and it’s like, “Okay, great, so that’s what you want to do, sounds good,” but then to your point, it’s like who are you competing against, and in addition to it being other people that call themselves B2B SaaS copywriters, it can also be a company hiring somebody internally, it could be the marketing manager there or whoever writing the content themselves, or it could also be doing nothing.
They may not decide to go ahead and do anything at all. So, that can also very well be a competitive alternative, from at least that client’s lens, right? And then from there, it’s more sort of trying to dig in, it’s like, okay, well, now that you understand who you’re competing against, like people and behaviours, your point, the next step is like, okay, what are your unique values or attributes that you can stand on your own as and be able to utilize that as part of your positioning exercise? Do I have that right?
Tiffany: Yeah, I would say, yeah, that’s pretty bang on. And it’s like — and like, I mean, yeah, to your point, even just talking about B2B SaaS copywriters, right? There [are] thousands of us and so when you’re talking about yourself as a B2B SaaS copywriter and if you run through a positioning exercise, you’ll develop your audience segments a lot better.
You’ll probably figure out, “Oh, I specifically want to go after health tech companies,” or, “I specifically want to go after fintech companies,” and even within those segments, segment again, segment again and again and again and then you’ll kind of find your niche customer and that’s not bad. People want to often go wide so that they don’t cut off opportunities for client work again, but going niche will help refine your messaging and really speak to those people that you do want to work with.
Mohammed: Yeah. I like your point. It could very well be something like B2B SaaS copywriter for healthcare companies in the United States or healthcare companies specializing in this specific thing so it’s super, super niche, but at the same time, once you are at that narrow path, it’ll also help you determine, it’s like, okay, who are all the people that fall under that bucket? Because then that’ll — that just becomes your pipeline.
Tiffany: Yep, exactly, yeah, and then you’re super targeted and you’ve cut out the fat and you know exactly who you’re talking to and you have your outreach list, for sure.
Mohammed: So, we’ve talked quite a bit about positioning. We’ve also talked about trying to get a better sense of not just what it is that you’re trying to provide but also who is it that may need it. And what are all the different things that they may compare you to when they’re considering who to go ahead with and utilizing that as well to sort of get a better sense of your value.
But then also getting a better sense of who should be in your sales funnel, rather than every single person that might need a freelancer, and utilizing that as a means to being much more tactical to growing and building your business. So, in addition to all of this, what other insights or advice do you have for Canadian freelancers?
Tiffany: This piece of advice has nothing to do with positioning but my other piece of advice would be to break up the day with exercise. That’s one of the things. I know it’s like just this kind of routine, day-to-day thing but you have freedom over your schedule and that’s one of the massive benefits of being a freelancer.
But breaking up the day with exercise is super, super important and it can recharge you when you are tired from working solo all day long and you haven’t spoken to another human being. So, yeah, that would be my number one piece of advice is to get up out of your chair and do some exercise in the middle of the day to kind of break up that day.
Mohammed: And I’d love to know where people can find out more about you and your work online.
Tiffany: Yeah. So, you can find me on Twitter. So my name is Tiffany Regaudie and I’m going to spell it out because nobody ever knows how to spell my name. But you can find me on Twitter at @tregaudie. Or check out my website at tiffanyregaudie.com. And I’m on LinkedIn. I’m on Instagram, @textualorientation so you can also find me there. I’ve kind of like — it’s a mix of professional stuff and personal stuff, my Instagram. But, yeah, that’s where you can find me.
Mohammed: Well, thank you so much for this opportunity to learn from you. I really appreciate you making the time to chat with me about all things positioning.