How to Win podcast with Peep Laja

Latest Episodes:

Landing Bigger Clients - with UserGems' Christian Kletzl Nov 06, 2023

Show notes

Summary

This week on How To Win: Christian Kletzl of UserGems, champion tracking software for sales. You'll hear the process they went through to find the product their clients were willing to pay for, how they make themselves appear bigger than they are, and more.

Key Points

00:30 - Appearing larger by using ads, content, LinkedIn, conferences

01:00 - Pivoting multiple times before finding product-market fit

01:30 - First customer paying $50k, taking 3 months to get second

02:15 - Becoming workflow company based on customer feedback

03:00 - Enabling workflows with routing, notifications, messaging

04:15 - Going sales-led to getting feedback and sales quickly

05:00 - Moving upmarket for better economics

06:30 - Creating more value like selling furniture over lumber

07:30 - Getting Salesforce access to enabling workflows

09:00 - Pushing workflow steps to driving success

12:00 - Workflow products having better retention

13:30 - Hitting $1M revenue in 12-18 months

14:15 - Clipboard Health pivoting successfully

16:00 - Testing crazy versions when growth stalling

19:00 - Appearing bigger through LinkedIn, ads, case studies

22:15 - Focusing on use case despite competitors

23:45 - Building moat with brand recognition and revenue impact

25:15 - Saying no to unfit customers

Mentioned:

Christian Kletzl's LinkedIn
UserGems

My Links:

Growing a SaaS Under HEAVY Competition - with Livestorm's Gilles Bertaux Oct 30, 2023

Show notes

This week on How To Win: Livestorm's Gilles Bertaux, a meeting and webinar platform. You'll hear how Livestorm succeeded despite many well-known competitors. How they got their first customers. And how they grew past $10 million in revenue.

Key Points

1:00 - How Gilles got the idea for Livestorm and validated it with customers
2:00 - Getting the first set of customers
3:15 - Reaching $1 million ARR in 2-2.5 years
3:45 - Growth during COVID-19 pandemic
4:30 - Differences between Livestorm and virtual event platforms
5:45 - Importance of recurring revenue products
6:00 - Anti-active usage products retention rates
7:00 - Differentiation in the webinar space
8:00 - European privacy laws advantage
9:30 - Messaging differentiation vs. business strategy differentiation
10:00 - Shipping features fast vs. carefully
13:00 - Prioritizing features based on positioning
14:15 - Strategy changes after hitting $10 million revenue
16:00 - Lessons learned over 7 years
17:30 - How Livestorm won

Mentioned:

Livestorm
Gilles Bertaux on X
Gilles Bertaux on LinkedIn

My Links:

Rebuilding the ICP - with Wonder's Guy Cohen Oct 23, 2023

Show notes

This week on How To Win: Guy Cohen, CEO of Wonder an on-demand secondary research platform. They built the company to 8M in revenue, realized their ICP was wrong, tore it down and rebuilt again. That's what we break down in this episode.

Key Points:
00:02:29 Failed many times, learned hard lessons, narrowed target.
00:04:28 Innovative marketing approach convinces lighthouse customers.
00:09:12 Canaries told us we were wrong, now what?
00:11:02 SMB business scaled pre-COVID but had issues.
00:14:54 Friction, pricing, and quality debated; race against time.
00:18:27 AI: Extinction risk or growth accelerator?
00:22:37 Voice to customer, sales, mistakes, choosing, committing.
00:23:40 Closing thoughts.

Mentioned:
Guy Cohen's LinkedIn
Wonder

My Links:

The Multi-Product Strategy - with Podia's Spencer Fry Oct 16, 2023

Show notes

Summary
This week on How To Win: Spencer Fry of Podia, the all-in-one platform for publishing, promoting, and selling content online. You'll learn how Podia succeeded in the face of heavy competition. Why the benefits of having multiple products outweigh the downsides for Podia. How Podia's long-term investment affects everything from product creation to marketing decisions. And more.

Key Points
[00:05:00] - Selling courses, downloads, and webinar access all in one place.

[00:07:45] - The long-term view is distilled across the entire team.

[00:10:45] - COVID led to their biggest month ever, 3-4 times bigger than before.

[00:14:30] - Having multiple products.

[00:20:30] - Website and email revenues compared to course sales.

[00:21:15] - Customer progression: from website, then email, before selling products.

Mentioned:
Podia
Spencer Fry on LinkedIn

My Links:

Selling 1000s of SaaS Startups - with Acquire's Andrew Gazdecki Oct 09, 2023

Show notes

Summary
This week on How To Win: Andrew Gazdecki of Acquire.com, the startup acquisition marketplace. You'll hear: How Andrew lands Times Square advertising to promote startups on his platform. How he went from doing everything himself to quickly assembling a team to speed up his company's growth rate. How he discovered a big opportunity to create a new company in the mergers and acquisitions market. And so much more.

Key Points

Marketplace launched by solo founder who works tirelessly. 02:04
Marketing showcased through creativity, cost-effectiveness, and social proof. 05:52
Personal experiences lead to a successful self-funded startup. 07:01
Team rehired, subscription model initiated, challenges faced. 10:44
Startup acquisitions streamlined using standardized tools and data-driven relevance. 13:39
Rapid execution guides towards the right direction. 17:27
User interviews standardized to analyze product usage. 21:47
Feedback sought, emphasizing negative comments, to nurture a customer-centric culture. 23:16

Mentioned:
Acquire.com
X/Twitter: @agazdecki

My Links:

Growing a SaaS by Launching a Service - with Boast AI’s Lloyed Lobo Oct 02, 2023

Show notes

Summary
This week on How To Win: Lloyed Lobo, founder of Boast AI, which helps companies find and claim tax credits from their R&D investments. LLoyed launched two different software companies, which failed. He followed it up with a service business, Boast, which took off.

You’ll hear why he thinks services are a better way to launch a company than software. We’ll dive into how he got his first customers by cold calling and we’ll discuss how he grew his company by publishing articles and organizing an event.

I’ll share how I used similar methods to grow my businesses.

Key points:

Start by selling a service to learn what to build and get good at customer success (00:36)
Pick an unsexy market that's not chased by trends (04:26)
Validate the ideal customer profile and problem through paid consulting work (04:55)
Product-market fit is when customers get an outcome and don't cancel (05:09)
Build the first product iteration with no-code tools (05:50)
Double down on what's working from 1 million to 10 million ARR (14:18)
Owned media like newsletters and events builds real relationships (15:35)
Alignment with co-founders and investors on values avoids issues (20:29)
Communication + creation + consistency drives success (21:33)
Boast won by starting as a service, focusing on one market, and building owned media (21:43)

Mentioned:

Boast.ai

From Grassroots to Greatness

Lloyed’s personal site

My Links:

Announcement: Summer Break 2023 May 24, 2023

Show notes

With summer around the corner, How to Win will be taking a brief hiatus. During this time, the team will be working behind the scenes to bring you more exciting insights from today’s top B2B SaaS entrepreneurs and CEOs when we return in Fall 2023 with a brand new season. In the meantime, catch up on past episodes of How to Win, and stay connected with me on LinkedIn and Twitter (links below).

Thank you for tuning in and supporting the podcast—I look forward to seeing you back here very soon.

My Links:

Cross-company collaboration with Pluralsight's Lindsay Bayuk Apr 11, 2023

Show notes

Summary:

This week on How to Win: Lindsay Bayuk, CMO at Pluralsight, an online technology learning platform designed to help teams upskill. Pluralsight was founded in 2004 and was acquired by Vista Equity Partners in 2021.

In this episode, Lindsay breaks down some of the strategies that have helped her as a CMO. We discuss communicating the importance of marketing to a CEO, how to align your company metrics, and why you should be wary of 'yes-men'. I weigh in on cross-company collaboration, the correct way to use customer research, and why a day not gathering customer intelligence is a day wasted.

Key Points:

Lindsay discusses what it's like being a CMO with a product marketing background (01:10)
Is life too short to work with a CEO who doesn't understand marketing? (03:10)
I dive into communicating the importance of marketing with a CEO with a quote from former Privy CMO Dave Gerhardt and Drift's David Cancel (03:51)
How does Lindsay communicate important marketing metrics cross-company? (05:38)
I talk about getting buy-in from across the company with a quote from Hubspot's Kipp Bodnar (09:31)
Lindsay lays out Pluralsight's successful messaging and positioning play (11:24)
I weigh in on how you should approach your positioning and messaging (13:34)
How does Lindsay use customer interviews to inform Pluralsight's positioning? (14:26)
I discuss how to use customer research in the right way (16:02)
How are Lindsay's teams structured and how does she juggle them all? (17:14)
I explain why you should surround yourself with people who challenge you with a quote from former astronaut Garrett Reisman (19:11)
Why does Lindsay think that "go-to-market is a team sport?" (20:54)
What are some of the mistakes Lindsay has made in her career? (22:24)
Wrap-up (23:48)

Mentioned:

Lindsay Bayuk Website

Lindsay Bayuk LinkedIn

Pluralsight Website

Pluralsight LinkedIn

Dave Gerhardt LinkedIn

David Cancel LinkedIn

Kipp Bodnar LinkedIn

Garrett Reisman LinkedIn

My Links:

Cultivating a growth practice with Mural's Lauren Schuman Mar 13, 2023

Show notes

Summary:

This week on How to Win: Lauren Schuman, VP of Product Growth at Mural. Founded in 2011, Mural was valued at $2B after their Series C funding round in 2021. Before joining Mural, Lauren served as Senior Director of Product Insights and Growth at Mailchimp.

In this episode, Lauren breaks down how she has steered Mural and Mailchimp toward cultivating a growth practice. We discuss finding the right problem to solve, the importance of experimentation, and why she hires curious people. I weigh in on the benefits of gathering qualitative data, why marketing is a game of attention, and the diverse potential of growth teams.

Key Points:

Why is nailing your ICP the most important part of building growth? (01:24)
How does Lauren find the 'right problem to solve'? (02:43)
How did Lauren use quantitative data models to make strategic decisions? (04:17)
I weigh in on the benefits of qualitative data gathering with a quote from Attentive's Brian Long (07:11)
Lauren talks about how Mural differentiates itself from the competition (09:22)
How has Lauren been using copy testing to improve Mural's website messaging? (12:36)
I discuss why marketing is a game of attention (13:35)
Lauren reflects on the importance of onboarding in a product-led tool (16:41)
I explain why motivation is more powerful than friction (19:49)
Lauren breaks down how Mural uses onboarding to increase customer understanding and motivation (20:26)
What is a painted door test? With a quote from Carta's Shubhi Nigam (22:46)
What did Lauren learn about building a growth team at Mailchimp? (23:45)
I weigh in on creating a growth team that excels with a quote from RockBoost's former founder and managing director Chris Out (26:34)
Why does Lauren look for curious people at the hiring stage? (27:52)
Wrap-up (29:39)

Mentioned:

Lauren Schuman LinkedIn

Mural Website

Mural LinkedIn

Getting more accurate customer feedback with Attentive's Brian Long

Shubhi Nigam LinkedIn

My Links:

Laying the foundation for long-term company alignment with Salsify's Rob Gonzalez Feb 27, 2023

Show notes

Summary:

This week on How To Win: Rob Gonzalez, co-founder and CMO of Salsify, a commerce experience management platform that helps its clients win on the 'digital shelf.' Salsify defines the digital shelf as: "The collection of diverse and rapidly evolving digital touch points used by shoppers to engage with brands and discover, research, and purchase products.”

Rob co-founded Salsify in 2012 and has grown the company to over 740 employees serving a roster of high-profile clients. Salsify concluded their Series F funding in 2022, securing $200M in funding which brought their valuation to over $1B.

In this episode, Rob breaks down some of the strategies that have helped Salsify win, and some of the mistakes they've made along the way. We discuss diversifying customer acquisition channels, promoting employee autonomy, and why you might be under-charging your customers.

I weigh in on the increasing costs of customer acquisition, transitioning to a multi-product team, and employee surveys.

Key Points:

Rob discusses the customer acquisition channels that worked in the early days of Salsify (01:21)
When is it the right time to change your customer acquisition tactics? (04:58)
I reflect on the rising cost of customer acquisition (06:04)
Rob discusses what he calls 'market engagement rate' (07:37)
What has Rob learned about being a multi-product company after Salsify's recent acquisitions? (09:29)
My thoughts on running a multi-product company with a quote from Okta's Chief Product Officer Diya Jolly (11:55)
What practical advice does Rob have for founders trying to create a positive work culture? (14:01)
I talk about surveying your employees with a quote from employee management expert Don Phin (16:48)
How do you reinforce a positive culture consistently? (18:24)
I discuss the benefits of increasing employee autonomy (24:13)
Rob reflects on Salsify's pricing strategy with a quote from the Tim Ferriss Show, featuring Andreessen Horowitz's Marc Andreessen (25:13)
Why does Rob believe the next ten years of marketing will be defined by community and not content? (30:14)
Wrap-up (32:04)

Mentioned:

Rob Gonzalez LinkedIn

Salsify Website

Salsify LinkedIn

The Digital Shelf Institute Website

The Digital Shelf Institute LinkedIn

My Links: