How to Win

Peep Laja

Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories. No fluff. No filler. Just strategies and tactics from founders, executives, and marketers. Learn about building moats, growing audiences, scaling businesses, and differentiating from the competition. New guests every week. Hosted by Peep Laja, founder at Wynter, Speero, CXL.

Introducing How to Win
Trailer 1 min 22 sec

All Episodes

Key Points: Jonathan talks about how and why he founded KlientBoost (01:14) Jonathan discusses the company's original plan for growing by building their brand (02:43) Jonathan gives his thoughts on how they differentiate themselves from other agencies with their design, their many published case studies, and their consistency in everything they do (03:20) I give my thoughts on consistency and word-of-mouth strategy (05:24) Jonathan talks about lead sources, and how most of it isn't directly trackable or attributable (06:26) Jonathan discusses maintaining quality control on their MQLs so that they only go after the best leads. I give my thoughts on making an offer that potential clients can't turn down in order to get them to sign up (09:08) Jonathan talks about how turning around their operations, training staff and systematizing the company is turning around their retention and revenue (10:45) I give my thoughts on improving operations and empowering your staff to make decisions (13:27) Jonathan talks about employee satisfaction and how retaining a great staff is a competitive advantage for them (15:28) I give my thoughts on building great teams and the experienced/inexperienced hire trade-off, with a clip from Jim Collins (18:25) Jonathan tells me how he doubled revenue from $10 to $20 million during Covid (20:34) We discuss reviews and how KlientBoost ensures they are top of their field in terms of testimonials, and how they have looked scientifically at potential clients' thought processes (21:47) I give my thoughts on reviews and how sometimes a bad review can make you seem more human and likeable, an example of Elliot Aaronson's Pratfall Effect (24:34) Jonathan talks about their ambitious company marketing goals for the next few years, including getting a Netflix series (26:26) I give my thoughts on ambition (29:23) Jonathan talks about their mathematically-planned strategy to hit $100 million in revenue (30:22) Wrap Up (33:05) Mentioned:GongZuoraDriftG2CapterraMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Dec 6

36 min

Key Points: Gina talks about how Mighty Networks adapted when their early customers were enterprise, rather than the SMBs or creators they were trying to attract (01.20) I give my thoughts on adapting to changing opportunities, and growth mindset (03:01) Gina talks about how they transitioned to their ideal customer base over time (05:00) Gina discusses how Mighty Networks specifically avoided competing with major social platforms by niching down and combining e-learning and community building tools (08:06) I give my thoughts on the value of having a voice and opinions as a brand (11:13) Gina talks about how they improve the product by rolling in requested features which fit their long-term brand strategy (12:45) Gina reveals how they have grown - and retained revenue - by building a flywheel of users joining a customer network, and then forming networks of their own (15:11) Gina reveals that their main inbound traffic comes from Google searches for website builders, not 'social media' or 'community' (16:34) We discuss how to avoid communities becoming ghost towns, keeping engagement high, and the value of a feeling of exclusivity, with additional thoughts from former Lattice VP of marketing, Alex Grech (17:57) I give my thoughts on forming breakaway brands which do things differently to create space in a crowded market (23:11) Gina discusses their B2B2C business model, and always doing the best for their customers, so they can give their customers in turn the best experience (24:27) I give my thoughts on being brand-first as a long-term competitive advantage (26:48) Gina talks about encouraging competition in the space to help build awareness among potential customers (28:54) Wrap up (32:25) Mentioned:NingDriftGongRefine LabsHubspotBasecampLatticeIkeaMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Nov 29

34 min 20 sec

Key Points: Guillaume talks about Lemlist's USP as email personalisation, rather than automation (00:54) I give my thoughts on feature-based differentiation as a way of breaking into a market (03.31) Guillaume talks about the company's exponential growth over the years (05:05) Guillaume talks about marketing, blogging and building communities on a lot of channels to build lead profiles and mental availability (06:37) I give my thoughts on building a social media presence as a newcomer to a field (08:41) Guillaume discussed Lemlist's transparency on social media, and learning with their audience to build a community (09:31) I give my thoughts on building a strong digital presence by holding strong, controversial opinions and powerful storytelling (12:17) Guillaume discusses tapping their community for feature ideas, and turning their engagement into a product advantage (13:14) Guillaume talks about the various ways the company built its presence in the early days (15:55) I give my thoughts on mental availability, with a clip from the term's creator, Byron Sharp (18:52) Guillaume talks about building the personal brands of Lemlist employees as experts in their own fields (21:18) I give my thoughts on company brands building up the personal brands of their people (24:01) Guillaume talks about Lemlist's strategy and having the confidence to be approachable, friendly, and not compare themselves to what the competition are doing (24:40) Guillaume gives his thoughts on niching down on SMBs, and not encouraging enterprise customers (27:54) I give my thoughts on focusing in on the ideal customer (30:34) Guillaume reveals where the company is headed in the years to come (31:59) Wrap up (33:46) Mentioned:HubspotSalesforceLinkedInByron Sharp My Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Nov 22

36 min 18 sec

Key Points: Neha talks about how Contentstack grew from a gap in a stagnant market and embraced new technology clients needed (01:13) I give my thoughts on championing change, and encouraging clients to come with you (3:08) Neha talks about how they took a product-led approach, building features the established competition couldn't match (5:11) I give my thoughts on pulling together and improving existing technologies to build a better product (6:44) Neha discusses how Contentstack was spun out successfully by keeping it separate from the main services firm (8:28) I give my thoughts on the difficulties of transitioning from services to SaaS (09:41) Neha talks about how the firm became trusted by investors (10:50) Neha talks about how their consultative and flexible approach helps them keep 99% retention (12:41) I give my thoughts on educating potential clients and seizing opportunities when launching new product segments (16:57) Neha gives her thoughts on how they win clients by improving on the poor performance and inflexibility of the competition (17:47) Neha talks about their network of partners as a moat, and how they will put clients in contact with other firms who offer features they can't (22:17) I give my thoughts on the concept of cornered resources, as defined by Hamilton Helmer (24:48) Neha talks about how Contentstack's strong expertise and consultative approach helps differentiate them from the competition (26:28) I give my thoughts on highlighting your advantages and marketing to customers who know what they are looking for (29:28) Neha talks about how they are planning to build a developer community/ecosystem to expand the features of Contentstack (30:31) I give my thoughts on community building, with a clip from Morgan Brown, VP of Growth at Shopify (32:29) Wrap up (34:50) Mentioned:HubspotSalesforcePipedriveShopifyMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Nov 15

36 min 4 sec

Key Points: Alina describes how Chili Piper identified it's niche and developed a solution to one client's problems (01:06) I give my thoughts on adding value, and how that shows in ARR (06:21) Alina talk about how leads were reluctant to try Chili Piper across the whole site, so they sold it as a low-risk experiment (08:01) I give my thoughts on businesses' reluctance to change, and selling them on experimentation (08:55) Alina describes how she networked hard and targeted influential figures and early adopters to get their first customers (09:26) I give my thoughts on using brand ambassadors, and look back to advice from Guillaume "G" Cabane of Hypergrowth partners from episode 10 (10:51) Alina describes how Chili Piper was able to create a product that Google and Salesforce couldn't, because they don't have the drive or specialist knowledge (11:50) Alina talks about how they are innovating to stay ahead of the competition now that the market is getting more competitive (13:56) Alina describes how their strategies are evolving over time (19:00) Alina discusses their 160% ARR, and how Chili Piper achieved the figure (20:05) I give my thoughts on client retention, and how it's become a key metric (21:08) Alina talks about how the business is changing, and relying on intelligent insights to make product decisions (22:25) I give my thoughts on using data to inform business decisions, but ultimately accepting that every decision is a bet (25:28) Alina gives her thoughts on Chili Piper's pricing structure (27:39) Wrap up (30:50) Mentioned:Customer.ioHypergrowth PartnersThinking in Bets - Annie DukeChili PiperSales ForceCalendlyMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Nov 8

33 min 3 sec

Key Points: Ben talks about how Privy struggled to scale in its original form (01:07) Ben explains how they developed the idea for focusing on email list growth (04:56) I give my thoughts on product vs distribution (06:16) I give my thoughts on freemium models, and showing users the benefit of paying for additional features (09:37) Ben describes how Privy differentiated itself from other e-commerce marketing tools (12:06) Ben talks about their early marketing efforts (13:19) Ben talks about developing integrations as a key part of their product (14:05) I give my thoughts on growing through app exchange marketplaces (15:47) Ben talks about moving from a partner of Mailchimp to a competitor (18:37) I give my thoughts on taking risks to attack the competition, and not becoming complacent (22:11) Ben talks about how Privy succeeded by niching down to a very specific target market, and keeping track of their needs (26:31) I give my thoughts on transient competitive advantage (28:06) Ben gives his thoughts on pricing themselves against the competition (29:17) Ben talks about Privy's future plans and strategy (32:51) Wrap up (35:00) Mentioned:ShopifyWixSumoOpt-In MonsterMailchimpSupermetricsSuperlemonMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Nov 1

36 min 12 sec

Key Points: Morgan explains Shopify's current pain points (01:07) Morgan explains how Shopify's ecosystem helps differentiate it (2:35) Morgan explains how Shopify's marketing targets potential business owners rather than B2B customers(3.48) I give my thoughts on Nassim Taleb's 'Antifragile' theory of attracting customers with a 'low risk, high potential reward' pricing model (5:04) I give my thoughts on using qualitative data to ensure you are targeting customers with the right messaging (6:55) Morgan gives his thoughts on lowering the barrier to entry for business (7.50) I give my thoughts on Richard Reynolds 'Good Strategy/Bad Strategy' theory, which suggests analysis of problems, not aiming for solutions, is the most effective way to plan (8.38) Morgan explains Shopify's long term goals and strategies - simple pricing, a product which can be adapted to suit the needs of every business, and solving the problems which matter to the most customers (10.35) Morgan explains where the business' core strategy of making e-commerce accessible comes from (15:15) Morgan talks us through Shopify's strategic planning process (17:05) Morgan gives his thoughts on staying ahead of the competition, and competing with the likes of Amazon (20:10) I give my thoughts on how to compete against a category leader (21:57) Morgan explains how Shopify tracks the competition's movements and strategies (23:16) Morgan gives his thoughts on Shopify's moats, and how it is maintaining its position (25:08) Wrap up (30:17) Mentioned:ShopifySpeed CommerceMagentoNassim Taleb - AntifragileRichard P Rumelt - Good strategy, Bad Strategy James Carse - Finite and Infinite Games My Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Oct 25

32 min 29 sec

Key Points: How G makes winning a repeatable science (02:38) How G starts establishing opportunities for growth (04:10) My thoughts on maintaining 'scent' and keeping pre and post-click messaging consistent to drive conversions (07:19) How G works with a client, step-by-step (08:20) My thoughts on how drift managed to lead by introducing a new narrative (11:15) G's thoughts on category creation and how to stand out whilst avoiding a feature war (11:55) My thoughts on successfully creating new categories by adding 'must-have' features (17:05) G's thoughts on establishing the full extent of your theoretical customer base (18:00) My thoughts on choosing the ideal market segment from the pool of potential customers (19:50) How G uses data to work out who to target and how to effectively communicate with them effectively (20:55) My thoughts on brand-based differentiation (or lack of) between competitors (25:35) G on how to ensure a connection with your audience using brand ambassadors (28:10) G on how to build up an insight-based customer persona in order to differentiate your brand and offer the right solutions (30:40) Wrap-up (33.40) Mentioned:DriftSegmentGorgiasGainsightG2OwlerForrester ResearchGartner Research My Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Oct 18

35 min 30 sec

Key Points How Lattice identified and focused on its niche through conversations with customers (01:55) My thoughts on how to enter a crowded market and find your space by attacking from below (05:00) How Lattice honed their marketing strategy and began interviewing big-name non-customers for their media channels, building a brand association (06:24) My thoughts on building mental availability with professional customers by keeping them in mind and engaging with them early, delivering them unique insights so you are a name they think of when they are ready to buy (07:57) How Lattice developed new products which threatened the existing major players, and their ongoing product strategy (09:09) How Lattice developed its culture around sharing success and caring about conversations, and the importance of that in a people-management platform (11:56) How Lattice managed to differentiate itself from its competitors by focusing on what employees needed, and building a non-sales focused community of HR professionals (14:24) My thoughts on building mental availability by placing yourself at the center of a user community, and leveraging that down the line (18:04) How Lattice managed to differentiate itself as a brand using distinct messaging once competitors caught up from a product perspective (20:54) My thoughts on hooking site visitors with great copy and design (23:18) How Lattice looked outside the box to market its product with books and billboards (23:50) My thoughts on introducing slight cognitive disfluency to your messaging, to force people to stop, think and notice you (24:29) How Lattice has managed to retain its customer base whilst targeting higher-worth customers, by providing messaging and support to both markets, and adapting its marketing and sales strategies (25:30) How Lattice has become more ambitious with its marketing as it has grown, taking larger, big-budget risks to build its community (28:21) Wrap up (31:15) Mentioned:Alex is now CEO and founder at Dock.usLatticeCulture AmpDavid Cancel (Drift)Clayton ChristensenMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Oct 11

32 min 59 sec

Key Points How Colin and Customer.io broke into their category (01:22) My thoughts on product-based differentiation (03:03) What game Customer.io is trying to win (04:34) How Colin is trying to differentiate Customer.io (05:47) Colin's thoughts on building and running a distributed company (09:06) My view on new ways of management (10:53) How Colin thinks about moats (12:40) Colin's take on the big players in his category (16:12) How Customer.io attracts tech-savvy buyers (20:30) My thoughts on competing through innovation (21:22) My advice on building a personal brand (25:35) Wrap up (28:27) Mentioned:TeslaLucidDriftIntercomMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Oct 4

29 min 44 sec

Key points: Why Ross originally decided to lean into content marketing (2:07) My thoughts on developing a strong brand (3:50) How Siege chooses high quality clients (7:21) How Siege attracts the best people to work for them (8:17) My take on the war for talent (9:14) How Siege's marketing strategy has evolved (15:13) My thoughts on how to become a top name in your industry (16:38) Why people want to follow people, not brands (20:45) How Ross thinks about creating moats (25:00) Why my view on "hiring for talent, training for skill" has changed (29:29) What strategies Siege are doubling down on (30:30) Wrap up (32:35) Mentioned:Content and Conversations PodcastSeth GodinDave GerhardtMy Links:TwitterLinkedInWebsiteWynterSpeero

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Sep 27

33 min 50 sec

Key Points: My thoughts on the agency business model (2:14) How Profitwell's original mission evolved (3:32) One of the best pieces of advice Patrick can give (4:17) My take on keeping your brand focussed (5:38) Key bets Profitwell made that didn't work out (6:49) The highest ROI campaigns Profitwell have run (8:58) My take on using standard playbooks (10:37) Patrick on the fine art of throwing shade at competitors (11:48) How Profitwell educates potential customers (12:40) My thoughts on having strong opinions (15:19) How Patrick thinks about building moats (18:20) The big bets Profitwell is making for the future (23:35) Wrap up (24:55) Mentioned:Pricing Page TeardownBoxed OutConvertKitMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Sep 20

26 min 7 sec

Key points: How Intellimize thinks about competing (1:56) Two key ways Guy thinks about differentiation (4:45) My thoughts on "job to be done" boxes (5:10) The third way Intellimize thinks about differentiation (9:07) How Intellimize's competitive strategy has evolved (10:51) What I think is the most power moat a business can have (14:45) How Guy thinks about building moats (15:52) My view on the power of having a narrow focus (18:20) What competitiveness really means (22:24) How often Guy thinks about the competition (24:00) My take on the best way to deal with competitors (25:30) Wrap up (31:34) Mentioned:Hot JarHubspotBernadette JiwaTeslaProfitwellMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Sep 13

33 min 6 sec

Listen and learn: The problem Unbounce was originally trying solve (1:14) My take on the risks of competing on features (3:30) How their industry became a race to the bottom (5:30) Why you should aim to be unique, instead of being the best (6:42) How Unbounce thinks about the competition (11:10) My thoughts on taking a differentiated position in the market (15:18) What category Unbounce are trying to create (20:54) My take on the power of category creation (21:14) What Unbounce are betting their entire business model on (24:47) Unbounce's secret sauce (31:17) Wrap up (33:44) Mentioned:UnbounceAnimalzMichael PorterChristopher LochheadMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Sep 6

36 min 2 sec

Listen and learn: How Chris knew Refine Labs was going to win as an agency (1:45) How I built CXL using inbound marketing (2:50) My thoughts on creating strategic narratives (5:00) How Chris used LinkedIn to land Refine Labs' first clients (7:24) What I mean by being "the best" (10:12) Why Chris focusses on brand, rather than being transactional (13:50) My take on building personal brands (14:20) Refine Labs' vision for the future (17:25) How agencies can differentiate (18:15) Refine Labs' plan to take on industry giants (20:47) How Chris thinks about building moats (24:05) Wrap up (24:20) Mentioned:Refine LabsState of Demand Gen PodcastMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Aug 30

25 min 41 sec

Listen and learn: Animalz's two biggest pain points (2:02) How the Animalz team found a vision for the future (3:10) The biggest strategic bet that Animalz placed (3:56) One of the hardest things to do in business (4:48) How Animalz elevated the perception of their brand (5:48) My thoughts on the power of market penetration (6:05) What I call "The Kim Kardashian Strategy" (8:50) What Devin's mentor taught her about using leverage (10:42) How doing the unscalable helped Animalz scale (12:54) My thoughts on doubling-down on your key differentiators (13:21) Animalz's strategy for the next 3-5 years (15:37) Mentioned:Animalz's BlogHubspot's BlogMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Aug 23

18 min 53 sec

Listen and learn: The best advice Nathan Barry has received in business (1:44) How ConvertKit differentiates from the competition (3:54) The specific marketing campaigns that helped ConvertKit go from $2000 to $100 000 MRR in a single year (5:27) How feedback from a high-profile customer helped ConvertKit position themselves in the market (08:26) My take on playing the features game (09:40) A killer feature on ConvertKit that I think is f***king brilliant (13:36) How ConvertKit uses storytelling in their marketing campaigns (14:20) Why ConvertKit is committed to radical transparency as a business (15:27) How Nathan thinks about creating moats (17:04) The single biggest bet ConvertKit is making to reach $100 million ARR (18:22) Mentioned:Pat Flynn / Smart Passive IncomeKatie Wells / Wellness MamaConvertKit's BaremetricsTim GrahlSquarespaceTeachableNerdyDataBuiltWithMy Links:TwitterLinkedInWebsiteWynterSpeeroCXL

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Aug 16

21 min 4 sec

How to Win is launching Monday 12th July.Hear how successful B2B SaaS companies and agencies compete - and win - in highly saturated categories.

Jul 7

1 min 22 sec