Love At First Try

Positioning is a decision, not a tagline & the truth behind the AI hype (w/ Anthony Pierri)

If you're a SaaS founder who keeps rewriting your homepage and it still doesn't feel right, this episode is for you. Anthony Pierri is the co-founder of Fletch PMM. He and his team have run their 2-week positioning sprint around 500 times for B2B software companies, which probably makes them the most experienced positioning consultancy out there. He's also one of the clearest, least jargon-filled voices on LinkedIn when it comes to marketing. We spent an hour going deep on what positioning actually is (and isn't), why so many founders are stuck running five go-to-market motions at once without realizing it, and what happens when you make a real repositioning bet — with stories from Klaviyo, Anthropic, a trucking analytics company, and even Taylor Swift. We also got into AI — specifically, what Anthony discovered when he stopped using chatbots and went deep into Claude Code. His take is the most grounded I've heard in months. No fluff. No frameworks for the sake of frameworks. Just one of the sharpest operators in B2B marketing talking shop. 💡 Steal these quick wins from Anthony 1. Test your positioning by putting it on the homepage Not a Google Drive deck. Not a Notion page. The homepage. It's the one asset everyone in the company has to live with publicly, which is exactly why agreement on it sticks. If your team can't agree on what should go on the homepage, you don't have a positioning problem — you have an unresolved strategic decision. 2. Stop defining your target market by firmographics Company size, headcount, geo — none of these signals tell you whether a company actually needs your product. If you're trying to win five use cases inside one customer segment, you're running five different go-to-market motions in parallel. Pick the one that ladders into the biggest opportunity and lead with it. 3. Don't validate a reposition by asking your best customers They came to you for the old story. They'll tell you not to change. Customer research is one input — not the only one. The bet sometimes requires alienating who you have to win who you want. 4. Stop treating chatbot output as real work Anthony's experiment: dropping 20 sales call transcripts into a chatbot got him a summary in 10 seconds. Looked great. Then he wrote a detailed instruction file for the AI on exactly how to summarize one call — took 2 hours to build, 5 minutes to run on a single call. The realization: the fast chatbot version was producing something that looked plausible without doing the work. If you're using AI for anything where accuracy matters, the painstaking version is the real version. 5. Build for where the AI is going to actually be useful: smarter automation Don't build your strategy around AI replacing your team. Build it around AI replacing the slow, manual workflows that already exist (the stuff you'd otherwise build in Zapier or hire a junior to do). That's where the real productivity lives today.

Designing for delight, reducing design debt & using AI to prototype faster (w/ Alicja Suska)

Alicja Suska has been designing SaaS products for 10 years. She's worked at Toggle, Sourcegraph, and now leads product design at Buffer. What caught my attention: she comes from an artistic background — illustration and animation. That shapes how she designs. Colors, composition, how elements work together — it comes more intuitively. But she admits the process is harder to explain: "I can reason why something is good, but I work more intuitively." 🧠 What you'll learn in this episode: 0:00 - Jim's intro  0:25 - Who is Alicja and her journey through Toggle, Sourcegraph, and Buffer 3:00 - Designing for vastly different users: solo creators vs enterprise teams 5:24 - How to define taste as a designer (and why delight is more practical) 9:44 - Why delight only works after you've solved the core problem 10:26 - How an artistic background shapes product design thinking 15:33 - Sketching and showing rough work early (not polished mockups) 17:45 - Using AI in the design process: what works and what doesn't 21:30 - Prototyping Buffer Insights with Claude: 40+ concepts in one project 29:24 - The shiny object syndrome: wasting time on overhyped AI tools 31:41 - Designing AI features without screaming "this is AI" 39:15 - Enterprise vs consumer: when to be transparent about AI usage 40:04 - Onboarding philosophy: get users into the product as soon as possible 43:12 - Buffer's experiment: showing the UI before asking users to connect channels 46:18 - Credit card upfront vs free trial: what the data actually showed 49:18 - Time to value: identifying the real aha moment (it might not be what you think) 52:09 - Design debt: how navigation bloat quietly kills your product 55:01 - Why you need a dedicated designer who owns the product long-term 58:57 - Process hack: weekly time-to-value brainstorming sessions 1:04:38 - "Release what you're proud of" — Buffer's shift away from shipping fast 1:08:46 - Alicja's favorite products right now and why 💡 Steal these quick wins from Alicja: Show the product UI before asking for commitment. Buffer stopped blocking users with "connect your channel" upfront. Now they show the calendar first. Users explore, then connect when ready. Less friction, more trust. Design your empty states like onboarding screens. Most users skip onboarding anyway. They land on an empty screen that wasn't designed for being empty. Make your empty states guide users to the next action — not just fill space. Run a monthly "time to value" session. Alicja blocks 1-2 hours monthly to brainstorm: how can we shorten time to value? No big project commitment. Just one brainstorm + one small dev task. Fixes pile up over time. Use Claude to prototype before devs write code. Alicja brainstormed 40+ feature concepts with Claude, then had it generate interactive HTML prototypes using Buffer's design system. The team could experience features before any code was written. Audit your navigation every time you add a feature. The default pattern is "add another tab at the top." Eventually you run out of space and unimportant things sit at the same level as critical ones. Review navigation with every addition.

Why great brands are stolen, not created — and how to find your visual direction w/ Zach Stevens

This is Love at First Try — a podcast for SaaS founders and developers who care about design but aren't designers themselves. Zach Stevens is one of the co-founders of Conversion Factory, a marketing agency that works with growth-stage software companies. He runs their design team and has spent years helping SaaS brands go from scrappy to polished — without losing what makes them unique. I wanted to talk to Zach because he's a growth-focused designer. He doesn't just make things look good — he thinks about how design serves the business. And in this episode, we get into how to define your brand's vibe, why stealing from the right references matters, and how to make sure your design supports your marketing instead of fighting against it. 🧠 What you'll learn in this episode: 0:00 - Intro 0:25 - Who Zach is and what Conversion Factory does for SaaS companies 1:00 - Zach's origin story: from almost joining the Marines to meeting mentors who shaped Amazon's brand strategy 4:45 - The difference between a designer who just makes things pretty and one who solves business problems 7:15 - Aphantasia: why some people can't visualize ideas and what it means for design 11:50 - How Zach defines taste as a designer 13:58 - The Gap by Ira Glass: why your taste develops faster than your skills 17:27 - Why great brands are stolen, not created — and how Liquid Death proves it 21:20 - How AI changes the role of creative direction (you don't need to draw it yourself anymore) 23:40 - When beautiful design hurts conversions: the Adeline website breakdown 30:06 - The fine line between design that serves marketing and design that's just art 34:35 - How to add humanity to SaaS websites without looking like a stock photo catalog 38:43 - Why the emotion you want to convey matters more than how technical your audience is 43:12 - The branding spectrum exercise: masculine vs feminine, luxury vs affordable, subtle vs expressive 47:09 - Brands on fire vs brands on ice: how to stay creative without losing consistency 50:43 - Why typography alone can completely shift your brand's vibe 53:53 - The Mentor Cruise rebrand: from utilitarian to premium using vintage Porsche ads as inspiration 1:00:04 - How much should founder taste influence brand direction? 1:04:04 - Zach's favorite products right now: Cora, Mile IQ, and ChatGPT for thinking out loud 💡 Actionable takeaways from Zach Steal these quick wins: Define the feeling before the visuals. Before picking colors or fonts, ask: "How do I want people to feel when they interact with my brand?" Everything else follows from that answer. Use the branding spectrum exercise. Map where your brand sits on spectrums like masculine vs feminine, luxury vs affordable, subtle vs expressive. It helps you spot mismatches before you start designing. Steal from what makes you feel the way you want others to feel. Zach's team pulled from vintage Porsche ads for Mentor Cruise because Dominic wanted that timeless, premium vibe. Find your reference points outside your industry. Design should serve marketing, not lead it. If your website looks amazing but the message gets buried, you've prioritized aesthetics over conversions. Copy first, then design around it. Add humanity carefully. Photos of people can make your SaaS feel more relatable — but only if the vibe matches. A playful brand like PostHog uses pixel art hedgehogs instead of faces. Match the emotion, not the tactic. Typography sets the tone. The same sentence in a geometric sans-serif feels modern and clean. In a serif with thick-to-thin contrast, it feels wise and nostalgic. Pick fonts that match your intended feeling. Stay between fire and ice. "Brands on fire" are chaotic — nothing matches. "Brands on ice" are boring and rigid. The best brands have consistency with room for spontaneity depending on context.

Why tactical playbooks fail & the money moments framework w/ Marc Thomas

Marc Thomas wrote an annual upgrade email for Senja that listed 10 stupid products you could buy with the $58 you'd save. A scarf shaped like a receipt. Random Amazon finds. People took screenshots and shared it on Twitter and LinkedIn. That's the kind of marketing brain I wanted on the podcast. Marc's path: magazine journalist → SaaS founder (live polling tool) → Head of Growth at Powered by Search (working with $10-100M ARR clients) → Growth at Podia → now independent lifecycle marketing consultant. What I appreciate about him: he doesn't look or feel like a typical marketeer. More playful, more artistic. He understands the fundamentals but puts a creative twist on everything. 🧠 What you'll learn in this episode: 0:00 - Intro 1:01 - Marc's journey from journalism to SaaS marketing 9:51 - Why tactical playbooks are dead by the time you hear them 15:25 - The Senja annual upgrade email that went viral 19:27 - How Podia found undervalued influencers in their own user base 26:07 - How Marc defines taste (and the Tony Wilson / Factory Records story) 31:00 - Habits for developing your creative taste 34:47 - Why filtering yourself kills your best ideas 37:49 - The "money moments" framework for lifecycle marketing 40:13 - How Podia restructured onboarding based on actual buying behavior 44:29 - Why you're probably not sending enough email (and the data to prove it) 47:31 - How many emails to send in an onboarding sequence 50:54 - The key emails every trial sequence needs 54:09 - Marc's favorite tools: Sunsama, Whisper Flow, Manus 💡 Steal these quick wins from Marc: 1. Separate strategic from tactical playbooks. Strategic = "emails help because people live in their inbox." Tactical = "do this exact LinkedIn ad format." Strategic playbooks stay valuable. Tactical ones are saturated by the time you hear about them. 2. Find your money moments. Any moment where someone could give you money or take it away deserves a dedicated email sequence. Not just onboarding and win-back. 3. Send pricing early. Don't wait. Day 2 or 3 of your trial, send an email explaining your plans and who each one is for. People don't look at your pricing page as much as you think. 4. Send more email than feels comfortable. At Podia, they went from 4 emails/month to 12. Result: 12% bump in paid conversions on email days, with a trailing effect for days after. Another client saw 60% revenue increase on email days. 5. Front-load your onboarding. Day 1 and 2 are the most important. Marc sends 2-3 emails on day 1 alone for some clients. Then taper off: daily for week 1, then less frequent through day 30. 6. Make your emails worth sharing. The Senja email worked because it was useful AND entertaining. Brand win + referral win in one.

12: How to build an experimentation culture (even with low traffic) w/ Lucia Van Den Brink

Lucia Van Den Brink has run nearly 1,000 experiments in 14 years. She's worked with 100M+ brands, founded The Initial to help companies build experimentation in-house, co-founded Women in Experimentation, and teaches at CXL. I invited her on Love at First Try to talk about something most SaaS teams get wrong: how to actually make data-driven decisions without overcomplicating it. This episode is for you if you've ever thought "we don't have enough traffic to test" or "A/B testing is too expensive for us." Lucia challenges both of those assumptions. 🧠 What you'll learn in this episode: 0:00 - Intro: what this podcast is about and who it's for 0:25 - Who is Lucia and why experimentation matters for smaller SaaS teams 2:59 - The real difference between random testing and building an experimentation culture 6:36 - Why experimentation is actually about scaling leadership (insight from Booking.com) 9:15 - What counts as an "experiment" beyond simple A/B tests 11:32 - How a news website validated a 6-month feature before building it 12:57 - Why starting with removing elements is one of the biggest growth levers 16:22 - How to validate your data before trusting any experiment 19:05 - How to prioritize what to test (and where to start) 21:34 - Why you shouldn't segment your tests when you're just starting 25:41 - How to measure the right KPIs (including delayed metrics) 31:28 - Why you should never measure just one metric 36:45 - Real example: reducing churn in the first two weeks with a get started page 43:10 - Why "obvious UX improvements" still need testing (the humbling 20-30% win rate) 48:09 - The biggest mindset shift from junior to senior in experimentation 💡 Actionable insights from Lucia: 1. Start by removing, not adding One of the biggest growth levers is removing elements from your pages. Most tools let you hide elements without code. Try removing a field, a section, or a step in your funnel. You'd be surprised how often less friction means more conversions. 2. Run an AA test before any real experiment Before you trust your data, run an empty test (control vs. control). This tells you if your tracking actually works. Skip this and you might be making decisions on broken data. 3. Measure multiple KPIs, not just one Pick a main metric, but always track 2-3 supporting metrics. If you're testing onboarding changes, measure signups AND activation AND delayed metrics like paid conversions. One number never tells the full story. 4. Consider negative testing Instead of building a big new feature to test, try removing the opposite. Want to know if onboarding calls help? Test what happens when you remove them. You learn faster and cheaper. 5. Calculate the business case for "losing" metrics Sometimes a test hurts one metric but helps another. If showing a phone number increases support calls but also increases conversions, do the math. The revenue might cover the cost.