#60: Struggling to get free trial users to upgrade? Do this

In this episode, Ryan is joined again by Jess Chilman, Head of Growth at Rocket SaaS, to share five high-impact ABM campaign tactics designed to help SaaS businesses move upmarket and close six-figure enterprise deals. From research outreach to direct mail, podcasts, events, and bespoke campaigns, they explain how to build relationships with C-suite decision makers, stand out from the noise, and create memorable touchpoints that convert. If you want to move beyond mid-market clients and start landing enterprise logos, this is the playbook.Takeaways:Start with the BFG framework (Buyer, Firmographics, Geography) to build your high-intent account listValidate your TAM and use intent signals (funding, hiring, leadership changes) to refine your ICP listCampaign 1: Research outreach – co-create content with your ICP via surveys, interviews, or advisory boardsCampaign 2: Podcast ABM – invite C-suite decision makers as guests to build relationships and authorityCampaign 3: Events – run low-cost networking breakfasts or private dining sessions to connect face-to-faceCampaign 4: Direct mail – send thoughtful, personalized packages (chocolates, handwritten notes, themed gifts) to create standout momentsCampaign 5: Tailored ICP campaigns – design bespoke plays around your target’s pain points (e.g., mystery shopping, funding celebration gifts)Align marketing and sales so every touchpoint has tight follow-upThese tactics work best together, creating multiple relationship-building touchpoints with decision makersJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan is joined by Janelle Amos, founder of Elevate Growth, to dive deep into the most common growth challenges facing B2B SaaS businesses today. Janelle shares her proven framework for scaling SaaS marketing and reveals the power of focusing on the entire funnel — not just individual channels. From pipeline acceleration to optimising messaging and the importance of listening to customer feedback, this episode is packed with actionable insights for marketing teams and business owners aiming to hit their revenue targets faster.Takeaways:Marketing efficiency is key: Over-analysing one channel without considering the bigger picture won’t drive growthStart by reverse-engineering your marketing goals and aligning them with revenue targetsBuild an evergreen closed-lost program to re-engage opportunities that slipped through the cracksTest and iterate your strategies — don’t just increase budget, improve efficiency firstMessaging is often the biggest barrier — ensure your homepage clearly explains what you do and who it’s forSOPs (Standard Operating Procedures) help scale predictable, repeatable processesThe Elevate Growth Framework: A 7-step process to drive efficient, repeatable revenue with measurable resultsReach out to Janelle via LinkedIn for more insights on the Elevate Growth FrameworkJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan dives into one of the most important levers for SaaS growth: your onboarding experience. Too many companies get plenty of free trial signups but fail to convert them into paying customers. Ryan explains what industry benchmarks look like, why onboarding often fails, and how to design an experience that drives users to activation. From signup flow and guided tours to gamification, personalisation, and email onboarding, this episode is packed with practical ways to increase your conversion rate and reduce churn.Takeaways:Average free trial → paid conversion = 15–25%; below 15% means something is brokenDefine your activation milestone (e.g. Slack = 2,000 messages; Dropbox = 10 files saved) and build onboarding around itKeep signup flows short — name, email, password; use Single Sign-On to reduce frictionUse guided tours, tooltips, and short videos to highlight only key actions (not every feature)Personalise onboarding for different roles or use casesAdd quick wins & gamification (progress bars, rewards, incentives) to keep users engagedProvide educational resources, but make them optional and easy to findAdd a human touch — personal messages or LinkedIn DMs can increase upgradesUse email onboarding flows (5–8 emails over 30 days) to re-engage inactive trial usersLeverage product data to spot drop-off points and re-engage before churn happensJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan breaks down the four essential growth channels that you should be leveraging for your SaaS business: Owned, Paid, Earned, and Partnerships. He walks through each channel, explaining what they are, why they matter, and how to optimise them to fuel growth. Whether you're a startup or scaling SaaS brand, this episode gives you a clear framework for prioritising and executing your marketing strategy to unlock rapid growth.Takeaways:Owned: Content you control (LinkedIn posts, blogs, podcasts, case studies) — foundational but slow to buildPaid: Ads that accelerate your reach — LinkedIn, Google, Meta ads for top-of-funnel and retargetingEarned: The credibility you can’t buy — reviews, referrals, case studies, testimonialsPartnerships: The multiplier — co-host webinars, guest posts, and create alliances for exponential lead genBalance all four channels — don’t rely on just one, or you risk stagnationEvaluate and score your business on each category to identify where to improveJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan reveals the one move that had the biggest impact on his career and business growth. It’s not a complex strategy, a funnel, or a new piece of tech; it’s a simple step anyone can take this week that can open doors, spark inspiration, and accelerate your journey. Ryan shares the three steps to making it work, two personal stories of how it transformed his trajectory, and why it might be the fastest way to get unstuck in your career or business.Takeaways:The biggest breakthroughs often come from the smallest, simplest actionsYou don’t need a huge budget or complex strategy to level upThis approach works whether you’re an employee or a founderRyan used this approach twice. He outlines them both - each time it led to massive growth and lasting partnershipsJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan explains why intent data is one of the most powerful tools in a B2B SaaS marketer’s arsenal. He breaks down what intent data is, the difference between first-party and third-party signals, how to collect it, and how to use it to align sales and marketing for maximum impact. From simple website visitor tracking to advanced ABM campaigns, Ryan shares practical ways to spot buying signals and turn them into high-converting opportunities.Takeaways:Intent data shows which prospects are actively considering solutions like yoursFirst-party intent = data you own (e.g., site visits, demo page views, webinar attendance, email engagement, in-product usage)Third-party intent = external signals (e.g., review site activity, funding news, hiring patterns, event attendance)Tools like AlbaCross and HubSpot can help identify and track high-intent website visitorsReview sites (G2, Capterra, TrustRadius) often offer paid intent data packagesSignals such as funding announcements, hiring for relevant roles, or leadership changes indicate potential buying cyclesEnterprise tools like Bombora and 6sense offer advanced, large-scale intent data (but at a higher cost)LinkedIn activity — profile views, follows, post engagement — can also signal interestSales and marketing must work together: sales to follow up directly, marketing to run targeted ABM/retargeting campaignsUpload intent-driven contact or account lists into LinkedIn Ads for highly targeted, high-performing campaignsJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan breaks down one of the most debated topics in SaaS marketing: pricing. Should you show pricing or not? What model should you use? From flat-rate and tiered plans to freemium, free trials, and usage-based pricing, Ryan walks through eight pricing strategies with real examples and tips for how to pick the right model for your business. If your pricing page is one of your most-visited — and least-converting — pages, this one’s for you.Takeaways:Showing pricing builds trust and qualifies leads — but there are trade-offsTry “pricing from” if you need a middle groundFlat-rate pricing is simple, but not scalable for all businessesTiered pricing (bronze/silver/gold) is most common, but can confuse buyersPer-user pricing is standard, but often gamed with shared loginsUsage-based pricing is great for technical platforms, but hard to forecastFreemium works brilliantly for top-of-funnel — if your product is stickyFree trials need great onboarding or users won’t convertCustom pricing suits complex/enterprise deals, but slows down the sales cyclePrice anchoring is a powerful way to nudge users to the plan you want them to chooseDon’t guess — test 2–3 models and see what converts bestJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan breaks down the anatomy of the perfect B2B SaaS website — from site map to homepage layout. With years of experience designing SaaS sites and running conversion rate optimisation campaigns, he shares what actually works to turn traffic into leads. Whether you’re planning a redesign or wondering why your paid ads aren’t converting, this episode is your go-to guide to building a high-performing site.Takeaways:Fix your website before investing in paid ads — otherwise you’ll burn cashYour site map should include: Homepage, Product/Solution, Pricing, CTA (Demo/Trial), Case Studies, Resources, Industries, and optional pages like Integrations or AboutDon’t overload dropdowns — keep navigation focused and clearYour homepage hero section needs one clear headline (≤10 words) and a strong visual of your productAvoid fluffy buzzwords — be clear, not cleverAdd trust signals: G2 badges, logos, testimonials, case study statsShow the problem before the product — connect emotionally with pain pointsUse the Z layout to present 3–5 key features with benefit-focused headlinesInclude a form directly on the homepage for higher conversionUse the FAQ section to offload dense copy and handle objectionsJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]

In this episode, Ryan shares the seven traits he consistently sees in SaaS companies that scale quickly — versus the ones that plateau or fail. After working with 100+ SaaS brands at RocketSaaS, he breaks down the mindsets, strategies, and behaviours that separate fast-growing companies from the rest. If you want to grow faster, smarter, and with fewer missteps, this is your checklist.Takeaways:Speed beats perfection — launch fast, learn fastEmpower your team — micromanagement slows everything downFounders should stay involved in marketing for real thought leadershipClear, narrow positioning always outperforms vague messagingMarketing budgets must scale as revenue scales (aim for 10% of ARR)Don’t obsess over attribution — understand demand generation holisticallyDeep customer insight (sales calls, transcripts, feedback) drives better messagingJoin the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected] 

In this quick-fire episode, Ryan runs through 15 practical, proven ways to generate leads and win customers for your SaaS business. From cold email that actually converts to creative ABM campaigns, referral tactics, content strategies, and more, this is a checklist for founders and marketers who need leads fast. Whether you’re pre-launch, post-funding, or scaling to your next milestone, there’s something here for every SaaS team.Join the SaaS Marketing Weekly Newsletter here: https://saasmarketingweekly.com/ Check out Ryan’s agency, Rocket SaaS, here: https://rocket-saas.io/ Send podcast guest pitches to: [email protected]