Positioning Puzzle VIP Days


90-Minute Power Sprints

Looking for a little help sooner rather than later?

Need support around tying key pieces of your brand together, or looking for feedback around a key offer or page on your site? 

Step into my office. Let’s get it done faster.

Ready to jump right in? Get in touch + get on my calendar here:

“I’m ready for my quick fix!”

"One of the best investments I've ever made in my business - and I have made A LOT! Hillary saw me, reached in, extracted, and catapulted. Hillary designed the trajectory of where I should take my business from where it currently stands... Hire her today."

(Shannon Matson, CEO + Founder, thesocialbungalow.com)

Let’s start with:

Positioning Puzzle Virtual VIP Days

A few reasons you might be a fit for a Positioning Puzzle VIP Day:

  • Maybe you’re overall solid with your current visual brand… but you’ve got a positioning problem! Maybe you’ve got a new offer coming out, your overall messaging is wildly outdated, or you’re prepping to speak to a new tier of client, etc! Now, you need a core concept to tie it all together that still fits with your current presence.
  • Maybe a lot has shifted in your business lately, and there are a ton of moving parts. You need someone who can comb through them all, and figure out how to make it all work together from a positioning standpoint.
  • Maybe you’re working on a new flagship offer, and want someone to dive under the layers and chaos with you, not only to help shape the offer, but to develop the key positioning touch points you can use for launches, copy, social, and strategy
  • Maybe you know there’s a level deeper to the work you’re doing, but you can’t see the forest or the trees. You need someone to go brain spelunking with you and hold you accountable to dig out how to frame your unique approach to your work.
  • Or maybe you’re planning a campaign/launch, and are sick of being the Chief Idea Officer. You need a pro in your corner who can comb through all the pieces with you, and hand you a document you can give over to your team to help them hit the ground running.

“Tell me more about the Positioning Puzzle Strategy Overview doc I get at the end!”

Your Positioning Puzzle strategy document is a clear, to-the-point overview that includes the following:

  • Audience overview (demo’s, challenges, goals)
  • Core offer(s) overview
  • Key differentiators
  • Problem we’re solving for
  • Solution we’re offering
  • Up to 3 proposed campaign positioning concepts (narrowed down to 1) that includes:
    • One sentence summary of the offer/brand
    • Quick fire summary (for social + interviews)
    • Concept overview
    • Positioning statement for the offer/brand
    • Elevator pitch
    • Language lexicon 
  • Content categories + angles
  • Visual tie ins (if applicable)
  • (One or two additional sections available by request, as needed)

“What will this strategy + doc help me DO exactly?”

  • It nails down the core idea that unites EVERY facet of your brand (and/or powerfully positions your new offer). That means you’re crystal clear on the “North Star” for this evolution of your business, and the message that will bring it to life in a powerfully differentiated way.
  • You’ll finally have an updated focus for your business that reflects where you are now, in a deeper way. You may changed a ton over the last 1-2 years, or be starting a new venture. I’ll help you bring those ideas neatly together in a “Yep, that’s it!” way, so you can name + claim your new evolution.
  • Beyond the concept – you’ll have fresh, catchy strategic language that you can use everywhere. You can pull anything you wish from the doc for your website, content, copy, interviews, and more.
  • You’ll be able to step into your next level at last, without worrying folks will be asking “… Huh?!” While you might THINK your brain is a hot mess, after over a decade in the industry, one of my superpowers is combing through huge amounts of info, and pulling magic from the mush. While I might see the concept before you can — my job is to help you own it, and love the ride.
  • You’ll have a baseline of whip-smart ideas you can hand over to your team, or dive into at will. Your ultra-potent strategy doc is designed to bring all your ideas together in a way that’s easy to see and communicate — so any time you need a fresh perspective, new idea, or jolt of clarity, you have a buffet of ideas available to jump into.

How does the day itself flow?

Format: VIP day, 11:00 AM – 5:30 PM ET

(Don’t worry, we work with international folks too — even you, Australia! Let us know your time zone and we’ll get it done with you. <3)


Prior documentation dump: We’ll be sending you an onboarding form (nothing too nutty, I promise) to bring me up to speed, and I also want you to send me eeeeverything else ya got, ideally by 48 hours before session at the absolute latest! 

Any decks/internal boards, any onboarding forms/applications you may have put together that are relevant, and any notes/documentation in service of the brand, data from the last launch, sales page, new stuff outlines etc. Client feedback/interviews and competitor analysis would also be killer if you’ve got it!

I’ll be combing through it all prior to the session so I’m ready to go with ideas before we even kick off.

(Call 1) Day-of Initial discussion (90 mins, 11 AM – 12:30 PM ET):

This is where we’ll go over all the notes and what I observed from your documentation, and my first-look ideas from your notes. These will be some ideas for positioning concepts, angles for your offers, audience, and message, stories we can tell, etc.

We’ll dig a little more into your differentiators, audience, approach, all that good stuff! 

Lunch break + concept development (12:30 – 4:30 PM ET):

I’ll go into my cave after our chat to start putting some options for positioning notes for the strategy/messaging together based on what we discussed. 

If I have any follow up questions/you have any follow up thoughts, we can discuss on Voxer!

Typically, I’ll send you the document I’ve developed 30-60 minutes before call #2.

(Call 2) Concept review + feedback call (4:30 PM – 5:30-ish PM):

I’ll present up to three concepts (though we usually hit on a key concept on the first call) to you for your review and thoughts — unless we decide there’s already a winner in the first part of the session, in which case I’ll be blowing that bad boy out. 

If we’ve nailed it, away we go! If not, we’ll go back and forth to workshop the concept, and hit on the next level idea. (This may be live on the call, OR we can hang up and I’ll head back to my cave to offer you a couple more ideas before we wrap.)

Final sprint (5:30 – 6:30 PM):

If necessary, this is where I’ll clean up the positioning statement docs and my notes for presentation, and get you all tied up and ready to go into your next phase!

Then, you take a deep breath, and revel in the clarity and cohesion we’ve created.

But if it still needs more tweaking?

  • We’ll make any additional edits over the next 10 business days
  • If there’s a major pivot needed, we can tack on an additional 60-minute call to discuss further contract options, and tack on up to 3 rounds of revisions crafted over two weeks.

Your investment for the VIP Day:


PIF preferred (but 2-part plans available)

Ready to jump right in? Get in touch to get on my calendar here:

"It's a game changer. I know you hear people say, 'Wow, that was the best investment I ever made in my business,' or 'Wow, this completely changed my life.'... but just having the clarity from Hillary in this session completely changed my approach to business. She's brilliant and amazing and I appreciate her insight so much!"

(Rachael Darden, Copywriter + Mentor, rachaeldarden.com)

Now let’s get into: 

The 90-Minute Power Sprints!

A few reasons you might be a fit for a 90-minute Power Sprint:

  • Maybe you have a THRILLING new offer about to launch and you want to hone into its most powerfully positioned form in the market. [Note: a sprint is ideal for key messaging ONLY, though I can offer minor tweaks to the offer itself! In VIP days, we can develop the offer together and position it too!]
  • Maybe your current site messaging (on one key page, i.e. Home, About, Sales, etc) that’s feeling pretty bleh, and needs a tune-up
  • Maybe you’re eyeballing/already working with a PHENOMENAL new tier of client, and want to massage a key page of well-positioned messaging to draw them in like a tractor beam of love
  • Or maybe you’ve got a big question on what’s next for the business, maybe even hit a bit of a wall — and you need a brain who understands your goals and the industry at large to hash it out

"Hillary spouts golden nuggets on tap and it was wildddd to experience how quickly she was able to see through the fog and call out - so clearly - what I do and why it’s awesome. Now my web copy is getting feedback like 'I physically said ‘woah’ out loud,' and 'That literally spoke to me so deeply… Take my card.' I am WOWED!"

(Caitlin Teixiera, Founder + UX Designer, caitiemeansbusiness.com)

These 90-minute 1-1 sessions include:

  • A quick onboarding form to bring me up to speed on what’s happening, so I”m not asking silly time-waster questions on the call ;) 
  • A 90-minute deep dive into your specific challenge (be it updating messaging, refining positioning, smoothing out the offer to get ’em ready for sale, and more!)
  • Up to 2 rounds of feedback for whatever you create after the session via Loom within two weeks. In other words, we discuss strategy on the call, you make the updates, send them to me within two weeks, and I’ll give you my feedback. Then, once you’ve applied that round, send it my way again for one last blast of TLC 
  • Recording and transcripts delivered to your inbox (my notes available on by request)
  • Any relevant templates offered up as needed

“What are some things I can walk away with after the sprint?”

  • A refined, irresistible focus for marketing your offer. I’ll ask you the questions that’ll open new ways of talking about your idea, and getting it in front of JUST the right people, so you bring in fab-fit clients, and feel confident your message is hitting all the right notes.
  • Clarity on exactly what makes you magical, and what you do beautifully for other people. It can be hard to read the label from inside the bottle! That’s why I’m here to help you zoom out, and see your forest for the beautiful trees it is.
  • Confidence in exactly what it takes to attract that higher-level person to you, because you’ve word-vomited a good chunk of your self doubt at my feet (not a requirement, but it does happen ;)), and we’ve parsed through it together, to help you see exactly why you’re so extraordinary, so you can move forward with clarity and chutzpah. 
  • “Whoa YES!” answers to your big business questions. Whether you’ve bumped into a wall or stumbled into a plateau, I can help you figure out what’s really going on, and where you really want to be heading, and how to get yourself on that road to greatness.

Your investment for the 90-Minute Sprint:


PIF preferred (but 2-part plans available)

Ready to jump right in? Get in touch to get on my calendar here:

Powerful Client Love

I did a VIP day with Hillary Weiss that basically changed the entire trajectory of my business…

“The actual foundation of what I teach in that proprietary program, and then the name of it and the isms and the language lexicon around it, and literally everything for my business has come out of one VIP session with Hillary.

I cannot even tell you the 10 fold ROI that a session with her is. She is so wicked funny, hyper-clever, hyper-attentive, goes through and understands you on a level that you can’t even see, and comes forward to the table with ideas mapped out thoughtfully. She really operates from radical care.

And the moment that you say something she not only gets it, but she comes back to you with intention and says Is this what you mean? Is this how we can do it? Is this exactly how it should look, sound and feel? And the answer is yes, better than I could have ever said it or thought it myself.

Hillary shows up for you and your success. She’s basically a vision editor and she pulls you into where you should be with your positioning and your messaging, and I cannot recommend hiring her highly enough.”

(Shannon Matson, CEO + Founder, thesocialbungalow.com)
Hillary was invested in my business as much as I am…

“Before working with Hillary my ideas were too out there and honestly I didn’t even know if what I was tossing around in my brain made any sense!!

It didn’t take long before Hillary was able to hear what I really wanted to be doing in my business and begin to piece it into something that was cohesive, made sense, stood out, and most important of all – excited me!!

I can be a little all over the place sometimes and Hillary never made me feel bad for it. Any time I would come to a call with doubt, she listened, gave feedback, and then I was back on the horse moving full speed ahead. I felt like Hillary was invested in my business as much as I am and that means a lot to me.

The best part was seeing our ideas coming to reality in the photoshoot. She absolutely knocked the creative direction OUT OF THE PARK! This was an experience I will never forget and will continue to move and build my business in the updated direction I want it to go.”

(Renae Saager, Body + Food Confidence Coach, renaesaager.com)
…she can somehow see YOUR special sauce SO clearly.

“When I first reached out to Hillary, I was really struggling to figure out what made me unique in a very crowded marketplace. I knew that my inability to articulate what made me different was holding me back from growing my business.

What’s amazing about Hillary is that she listens to you speak about a business that you think is fairly ordinary and she can somehow see YOUR special sauce SO clearly. She has this ability to take the things you haven’t been able to articulate – and all of a sudden – BAM – you have this genius concept all wrapped up in a crystal clear bow. It made me realize I didn’t have to work SO damn hard all the time to differentiate myself.

Oh- and Hillary is freaking FUN. She brings the fun – so it took away all the “shoulds” and the bullshit of how things were “supposed to be”. We got to play and discover and have a damn good time.

It’s been a huge year of growth for my business and I’m super excited to launch my group program this fall and scale in a way I never could have without her guidance.”

(Michelle Pollack, Leadership Coach, michellepollack.com)
At this point I’ve quadrupled my income since starting with her (and sometimes that’s a low month).

“When Hillary says power position, she means it.

I felt like my industry’s hidden secret for so long, like I was so close to the kind of growth and success I wanted, but it felt like I could never just clarify the magnitude of what I did enough to get there.

Signing up with Hillary wasn’t even a question. It was a full body yes.

We’ve been together for two years, and I’m not going anywhere because she’s always right there by my side, giving me the room to dump my creative mind in front of her, and she supports me in how I bring it forth into the world.

At this point I’ve quadrupled my income since starting with her (and sometimes that’s a low month).

At every stage in my business as I grow, I get to this point where even as a business coach, I’m like “do I still need a coach?”. The answer I always come back to is that I don’t need anybody, and I love Hillary. It’s a constant yes to Hillary. Because anyone can hire a coach, but nobody does business like she does.

(Rachel Turner, Business Coach, rachelturner.com)
…working with Hillary is freaking fun.

“My business moved faster in our 12 (extended to 24 because I can’t let go) weeks together than it had in YEARS.

The homework is focused, and strategic, and specific to *me* and my business, so I know I’m not wasting time throwing darts and hoping it hits a target. I can babble, and magically, she’s able to find the value in what I’m saying, reflect it back to me, and make my own thing sound amazing.

Also, working with Hillary is freaking fun.

I completely transitioned my business and business model. I used to do retainers and I was burning out, but stepping away from that meant stepping away from 75% of my income. Surprise but not surprise — I transitioned with no loss of income at all. I’m doing what I’m good at in a way that I enjoy, and I didn’t have to sacrifice money to do so.

I’m able to take random Thursdays off. I wake up without an alarm. My heart doesn’t jump at Slack messages anymore. I’m hanging out with my family in the middle of the day (that is, if I’m not napping).

I am so, so happy to run a slow-paced business. And when I *am* working, I’m in the zone and energized, because I’m doing stuff that lights me up.”

(Mikli Feria Jorge, Tech and Automation Strategist, heymikli.com)
…That’s an expected 5x return on our work together in a matter of 2 months!

“We all know “Cobbler’s Children’s Syndrome” is alive and well in the consulting industry. I can always more easily dream & strategize, plan & apply excellent marketing strategy for our clients, while struggling to find the clarity of positioning in marketing of my own…

… but the fear remained: would I regret spending money on Power Position Coaching? Shouldn’t I just set aside the time to do this myself?

Hillary has the aptitude and the resolve to listen intently to your challenges and ideas, and to reflect back what she hears, connecting it to practical applications in your business. Her advice prompts in-the-moment changes to your ways of working and communicating with ideal clients, just as it allows for larger, sweeping changes that will improve your work and real life.

During our time together, I was able to quickly implement changes to our services that I had been stalling on for years, and before her coaching was complete, I had already booked one new client for our new premium-priced marketing plan, PLUS had one additional ideal client in the proposal stages for the same service. That’s an expected 5x return on our work together in a matter of 2 months!”

(Amy Jacobus, Online Marketing Strategist, amyjacobus.marketing)
…I multiplied my investment in Power Position Coaching so easily.

“I LOVED that Hillary helped me uncover and refine what was already there. The encouragement, exercises, etc that she gave me were so valuable. And just having someone with her experience as a guide was phenomenal. I felt I was in great hands.

I booked 3 clients for my refined offer based on the framework that we worked on together as we were wrapping up. I multiplied my investment in Power Position Coaching so easily.”

(Mariana Durst, Brand and Business Strategist for Fine Artists, deskanddesign.com)
…I made back double my investment after the first 2 sessions.

“I couldn’t wait to actually create a consistent through-line for my brand. I was headed in A direction, but I wasn’t sure it was THE best direction. I’d been following Hillary for a while, and I love how she bleeds her brand. I knew that she could help me do that, and tie it all into a signature framework that people would just “get.”

Before working with Hillary, I launched a new program all on my lonesome. It was very successful, but I secretly thought it was a fluke. I didn’t know if that level of success was repeatable, or how to do it. I thought I’d had my ONE good idea and spent it.

Hillary guided me to my own conclusions. She didn’t just give me her opinion and sell it to me as the gospel. She listened and asked questions that pulled out what I just couldn’t articulate on my own.

I made back double my investment after the first 2 sessions–even after 5xing the price of my program. I also had people salivating (PLS keep this word. lmao) over my new offers before I’d officially launched them.

Fun note: My shiny new framework was copied too, so Mama I made it? Lol”

(Katie Pannell, Copywriter, katiepannell.co)
…Hillary has this fierce ability to help you stand outside of yourself and look at your experience, skills, vision objectively.

“I was massively excited to have Hillary’s eyeballs on my business and to be guided by her street smarts and creative cleverness.

I’d been feeling in a rut, struggling to articulate what work was and wasn’t lighting me up in my business anymore, what I actually wanted to do, and how to get out of the trading hours for money conundrum that was sucking up all my time and not allowing me to reach my revenue goals. I knew that Hillary would be able to help me make sense of all this in a way that would be truly aligned to me.

Hillary has this fierce ability to help you stand outside of yourself and look at your experience, skills, vision objectively. Of helping you to see your worth and the value you provide. Of helping you to package your magic up in a way that will position you powerfully in the market place with confidence.

While I’m still partway through this journey with Hillary, I am already SO fired up with excitement about the future of my business. I’m already starting to introduce my new positioning and messages to the world and behind the scenes I’m creation mode – opt-ins, packages, and more.”

(Hayley Maxwell, Copywriter, hayleymaxwell.com)
…my launch brought in a cool $18.5k, not to mention the 1:1 clients that have signed up since then thanks to my increased visibility.

“Hillary in your corner 100%! Whether I needed some quick advice when I was launching or was a little unclear on offers, she was a total cheerleader meets guidance counselor in the best way. (With a side of quirky drama girl too, obviously.)

Thanks to the framework I created with H, I was able to move forward with my first ever launch. I ran a 5 day challenge that had more than 550 people sign up and did my first webinar that had more than 150 people sign up…combined, the two tripled my email list! Plus my launch brought in a cool $18.5k, not to mention the 1:1 clients that have signed up since then thanks to my increased visibility.

I know that with the framework we created, I’ll be able to launch more offers, raise my rates, and overall kick ass in my business because I am able to clearly communicate exactly what I do for the first time.”

(Jenn Robbins, Conversion Copywriter, Jennrobbins.com)
…Working with Hillary has been a *blow-my-freakin-socks-off* experience.

“Here you go… though you can literally say anything. This has been the best experience ever

Where do I even start? Working with Hillary has been a *blow-my-freakin-socks-off* experience… since we started our 1:1 sessions she’s completely changed how I feel about my brand, my business and my skills as a copywriter. You need to find that person who can look at who you are and what you do from the outside in… and for me, Hillary is that person. I’ve struggled to articulate what makes me stand out from the sea of other writers… Hillary did it in one session. Best GD money I’ve EVER spent.”

(Emma Boshart, Email Copywriter + Story Strategist, creativeuproar.com)
…I (almost immediately) made my investment back and then some from the work I did with Hillary.

“It would be too boring to just say that I (almost immediately) made my investment back and then some from the work I did with Hillary. Because the process she led me through was not only completely business-changing but incredibly FUN, enlightening, and honestly, one of the most rewarding—financially and otherwise—experiences I’ve had in my business.

I’m making more money than I ever had and feeling so rock solid with where I’m headed. Setting boundaries like a boss and overall getting more done and showing up soooo much more and at a higher quality than I did before working with Hillary.

If you’re thinking of working with her just freakin’ do it.”

(Sarah Zerkel, Writer, sarahzerkel.com)
…I was most excited to have someone help me sort out my gazillion ideas and define what my super-secret power really is.

“Honestly, I was nervous that I was not coachable! I’ve done coaching before and felt like maybe something was wrong with me because I still couldn’t really nail what my positioning was.

I loved the concrete action plans and steps after every session. I did not complete some of the steps, but I do know exactly what I need to do once I launch the damn thing that I want to launch! I loved how Hillary made sure that I was not overly giving of everything I’ve ever learned in one program, and she helped me narrow down and simplify it without it feeling like I was taking out the value.

She is so witty, funny and smart! I love how her brain works and how she is able to make things easy to understand and create a solid foundation for everything I do from now on.”

(Lexi Smith, Cosmic Brand Coach, wanderwithlexi.com)
…Hillary will serve you a straight-up solution, all you have to do is follow her advice.

“Having Hillary as a coach is like having a new best friend…only this best friend is one of the most talented copywriters in the universe, and she knows her sh**. She shows up 100% as your coach, ready for whatever you bring her, with wisdom and without judgement. You can be the hottest mess ever, like me, and Hillary will serve you a straight-up solution, all you have to do is follow her advice. Best of all, she SEES you. Hillary helps you believe in a better version of yourself, and she practically paves you a yellow brick road to show you exactly how to get there. I’m doing things now that I was scared to do a few months ago because of the work we did together.”

(Melanie J Sparks, Conversion Copywriter, melaniejsparks.com)
…There was a lot of head trash that came up. Having support around that was key.

“I was concerned about my success in making a change after working so long in my previous industry.

Shifting services and positioning isn’t just communication and marketing, but also mindset…And there was a lot of head trash that came up. Having support around that is key.

Hillary is realistic and doesn’t give false hope or make “big” promises.

With her guidance, I launched my small business program which more than paid for our work together. Now, I’ve got a visual brand I’m proud of.”

(Alison Tedford, DEI Consultant, alisontedford.com)
…Hillary is super fckn smart, fun, funny, insightful, and asks GREAT questions that challenge your thinking and JOSTLE OR SHALL I SAY JOCEL your creativity ;)

“Working with Hillary: I got suuuuuper clear on my message and offer and Hillary somehow managed to get me to SIMPLIFY and stick to ONE thing (to start with). She gets how fast-idea-easily-distracted brains work and let me play in idea land without getting caught up in some helium ride adventure into never-never land as I’m apt to do when left to my own devices. Instead, she got me focused and even excited whattttt about putting my new 1:1 offer out, using a framework that felt truly like ME.

Part of what attracted me to Hillary (aside from her incredibly joyful and infectious presence) was the fact she had serious writing chops and knew what it was like to run a successful copywriting agency. As I was making the transition to brain coach from brand strategy and story consultant for these big ol’ multi-billion dollar companies (which got pretty financially comfy AKA SCARY TO SAY GOODBYE TO), I knew Hillary would get where I’m coming from and what it’s like to make a big shift.”

(Jocelyn Brady, Brain Coach, scribestorystudios.com)
…I’ve just had my first 5-figure month since I PIVOTED, which feels pretty darn fabulous…

“For me, it was less about the £££ than it was about finding my purpose and creating a life in which I do work I love, and much much less work I don’t love. And we have achieved that. We also created more £££.

I’ve just had my first 5-figure month since I PIVOTED, which feels pretty darn fabulous. More, though, I am happy in what I’m doing and I know I’m great at it.

And—after my needs and wants are met—that’s priceless. Of course, money is important, we need it, but that wasn’t the primary reason I sought Hillary out :D)

She’s so much fun…And enthusiastic – helping you be the best possible you that you can be. Best cheerleader and zany brain ever.

I’m much more confident now. I had a few wobbles of course, but as we worked through everything and made a plan and executed it, my self-belief skyrocketed.”

(Vicky Fraser, Author + Book Strategist, moxiebooks.co.uk)
…I created a minicourse and sold it the first time for almost 10K…

“I was absolutely amazed about how clear I got with my messaging, my pillars, and my strengths, and I finally have it together to talk about my business and my work beautifully.

So glad I finally made the decision to look deeper into my positioning to create a brand I adore.

With Hillary’s wisdom about copy, branding, and messaging, it feels like I’ve found a superweapon.”

(Sandra Janke, Business Mentor for Artists and Musicians, sandrajanke.com)
…I knew it would be fun to work with Hillary, but not THAT fun!

“Her huge personality and whip-smart marketing chops made putting together my new offers exponentially more fun than it would have been otherwise.

It was SO validating to have her support and hand-holding that my ideas actually were good and filled a unique need in my niche. I feel like I have a solid forever-foundation to build my business on.”

(Natalie Taggart, Launch Coach + Copywriter, natalietaggart.com)