Mastermind Recap for Sep 23-25, 2025

This week we hosted four SaasRise masterminds -- all with CEOs & founders of SaaS firms with $1M to $100M in ARR.

Here are the topics we covered this week...

1. Outbound Prospecting Strategy
2. Email Newsletter Scaling
3. Marketing & Growth Channels
4. Product Redesign & Onboarding
5. Managing SaaS App Time-to-Value (TTV)
6. Multitouch Attribution
7. Data Storage & Hosting Costs
8. Scaling Paid Ads & Video Campaigns
9. SaasRise Done-With-You Growth Program
10. Build vs. Buy: When to Acquire

⬇️ Below is the weekly recap of advice and recommended SaaS tools from our members, hope it's helpful!

All the best,
Ryan Allis at SaasRise
The Community for Experience SaaS CEOs & Founders

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Mastermind Recap for Sep 23-25, 2025

What Our Members Discussed This Week on the Live Calls

Topic 1 - Outbound Prospecting Strategy

Challenges:

• How to scale cold email outreach for B2B prospecting
• LinkedIn hits a hard ceiling on connect request volume (100 per account per week)
  

Advice:

• LinkedIn direct reach out is gold for higher-ticket sales, but it caps fast—use HeyReach to spin up multiple profiles without burning them.
• Don’t blast from your main domain—spin up separate ones and keep deliverability clean.
• Instantly is a great tool for cold outreach - keep to a max of 30 emails per day per inbox.
• Pair cold email with retargeted social ads. Seeing your name pop up in multiple channels keeps you top of mind.

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Topic 2 - Email Newsletter Scaling Compliance

Challenges Discussed:

• Platforms (BeeHiiv, Brevo) flagging or suspending accounts if you add in cold lists directly without warming up the leads and getting them familiar with your brand first
• Figuring out how to message existing customers without opt-in drama.
• Avoiding spam traps, blacklists, and GDPR headaches.
  

Advice Given:

• Don’t upload cold leads straight into newsletter tools. Warm them with tools like Instantly or SmartLead first, then migrate the ones who actually engage continually → that way they know who you are first and are familiar with your brand and content.
  
• The key is never bring people into a warm email platform (Brevo, Klayvio, MailerLite, BeeHiiv) etc. until they know you are and have demonstrated real interest in your product, service, brand through a history of engagement.
  
• Always keep clean documentation on how you got/built the list. If they ask, you want to look organized.
  
• Send out your email marketing from a different domain so you don’t put your main brand deliverability at risk.
  • Main domain = transaction emails + customer communications only
  • Newsletter domain = warm marketing emails only
  • Cold domains = cold marketing emails only
    
• Always keep backup warm email platforms running so a compliance hiccup doesn’t tank your campaigns.
  • Be sure you’re emailing your engaged subscribers at least 1x per week if not 2x per week
    
• Automate re-engagement emails so inactive leads don’t just die on your list.

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Topic 3 - Marketing & Growth Channels

Challenges:

• Scaling customer acquisition

Advice:

• Don’t pour cash into ads until your product and funnel are tight—you’ll just amplify leaks.
• Build small WhatsApp/Slack communities around your users; they convert better than cold ads.
• Affiliates can be a quick way to get leverage without building a huge sales team.
• Use smart triggers like competitor price changes to kick off timely outreach—way more effective than generic campaigns.
• Use AmpleMarket to message people when they post about your competitors or topic

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Topic 4 - Product Redesign & Onboarding

Challenges:

• Clunky UX and half-baked onboarding kill conversions.
  

Advice:

• Redesign your product UI/UX and make it great before you dump fuel on the fire. Ads will just magnify a bad funnel.
• You can redesign your existing UI with Google AI Studio or Claude.
• Onboarding should walk people to the “aha” moment fast—guide them through connecting their tools step by step.
• Use Webflow or something lightweight for quick testing instead of waiting on dev cycles.
• Upgrade your database now if you know you’ll need scale or ML features later—it’s painful to retrofit.

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Topic 5 -Managing Long Time-to-Value (TTV)

Challenges:

• Customers wait months to see results, and they start questioning the buy.
  

Advice:

• Don’t let silence kill the deal—send them a builder’s kit or “behind-the-scenes” updates so they see progress.
• Celebrate small milestones along the way.
• Get clients involved in dependency tasks early so they feel invested.
• Pre-buy or pre-build pieces of the process to shave weeks off setup.

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Topic 6 - Multitouch Attribution

Challenges:

• Too many tools for attribution/analytics across brands.
  

Advice:

• HockeyStack is a leaner Hyros; HubSpot is fine if you’re B2B and don’t want to overcomplicate.
• Cometly is an even easier to use version of Hyros
• Run PostHog for product analytics if you need deeper data.

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Topic 7 - Data Storage & Hosting Costs

Challenges:

• VMware licensing hikes and hosting bills creeping up.
  

Advice:

• Dump old data into cheaper S3 archival tiers.
• BunnyCDN is dirt cheap and solid for caching and streaming.
• Cloudflare’s storage can backstop you if you need redundancy.
• Design your stack so you can move providers quickly—no single-vendor lock-in.
• Ask providers to waive transfer fees if you’re migrating big chunks of data.

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Topic 8 - Scaling Paid Ads & Video Campaigns

Challenges:

• Scaling Meta ads is tricky—even with traffic and conversion data.

Advice:

• Don’t double budgets overnight—scale by 10–20% per week max.
• Test Meta’s Advantage Plus with super broad targeting once you’ve got enough conversion data.
• Run parallel campaigns with different conversion events—it keeps learning data clean.
• Retarget YouTube tutorial viewers with quick, punchy videos that drive the next step.
• Copy your Google Search campaigns into Bing to get an extra 10-15% of customers from paid search
• Get competitor keyword data from SEMRush

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Topic 9 - SaasRise Done-With-You Growth Program

Challenges:

• DWY program minimum ACV is $1000 as it works for mid-market and enterprise firms
• Growth program works, but takes months and a bit of team muscle.
  

Advice:

• Focuses on ABM lead list building, AI personalize outbound emails, and digital ad scaling on Meta, Google, Bing, Adroll and LinkedIn
  
• Growth program builds real marketing and growth infrastructure and systems—it’s not an overnight hack. Expect 3–6 months before you feel the lift.
  
• Once it’s running, ongoing costs are light. The system keeps paying back if you stick with it.
  
• Learn more at http://saasrise.ai/growthprogram

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Topic 10 - Build vs. Buy: When to Acquire

Challenges:

• Shiny object: acquire a small startup for features vs just fix your product.
• Switching from monthly to upfront payments.
  

Advice:

• Don’t chase acquisitions if your funnel is leaking. Nail trial-to-paid before adding new headaches.
• If you do consider a buy, weigh the cost of building from scratch vs integrating another stack—it’s rarely as easy as it looks.
• Push for annual contracts with discounts; break them into 6-month payment plans if cash flow is a blocker.
• Money-back guarantees lower the barrier but make sure your ops can back it up.
• End of year (Q4) is when budgets burn—close annual deals then.

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Tools Recommended This Week by Members

Outreach & Lead Gen

• HeyReach – LinkedIn outreach automation
• Instantly – Cold email outreach
• Apollo – Lead gen / outreach / contact data
• RocketReach – Contact data collection
• LinkedIn + Copilot AI – LinkedIn connection building
• Clay – Outbound orchestration & data enrichment

Email Marketing Platforms

• Brevo – Newsletter platform
• MailerLite – Customer newsletters
• Flowdesk – Newsletter alternative
• Drip – Newsletter alternative
• MailChimp – Broadcast email campaigns
• Beehiiv – Newsletter platform
• Transpond – Backup newsletter option
• Klaviyo – Email marketing

Analytics, CRM & Attribution

• HockeyStack – Attribution and analytics
• PostHog – Product analytics
• RB2B & Vector – Visitor tracking (US-focused)
• HubSpot – CRM & attribution (not ideal for cold outreach)

Development & Content Tools

• Webflow – Site management & A/B testing
• Jasper.ai + Zapier – Content automation
• Lovable AI – Slide deck creation/design
• ChatGPT – Content transcription & structuring

Infrastructure & Data

• Multiple inboxes/domains – Scaling cold outreach
• Data broker services – Lead lists (e.g., 100k leads for $600–700)
• BunnyCDN – File caching & video streaming
• Amazon S3 – Cloud storage
• Cloudflare – Storage & delivery

Ad Platforms

• Google Ads
• Meta Ads (FB/IG) and Advantage Plus – Facebook algorithmic advertising
• Bing Ads
• LinkedIn Ads
• Adroll Ads

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Growth Tools We Often Recommend:
Clay, Instantly, Apollo, ListKit, Cometly, Amplemarket­

Join The Community

We’ll be back in touch in a few days with another article on rapid SaaS scaling and exit prep. In the mean time, check out our SaaS CEO & Founder Mastermind community, SaasRise.

About the Author

Ryan Allis

Ryan Allis built iContact as CEO/Co-Founder from startup to $50M in ARR, 70,000 paying customers, #81 on the INC 500 list, and an exit for $169M to a publicly traded company.

At iContact, he raised over $45M in venture capital (including $15M in founder liquidity). Today, Ryan is the CEO of SaasRise, the #1 community for experienced SaaS CEOs and Founders with $1M to $100m in ARR.

Ryan focuses on helping tech and SaaS firms achieve 9 and 10 figure exits. He has coached the CEOs of Instantly, Clearstream, Seamless.ai, Tatango, Fuse, Pipeline, RNL, Retreaver, YouCanBookMe, Noteefy, RXNT, and many more growing SaaS firms from $5M to $160M in ARR. Ryan holds an MBA from Harvard Business School.

Apply to join our three mastermind communities.

• SaasRise - For SaaS CEOs & Founders with $1M+ to $100M in ARR
• GrowthRise - For B2B Marketing Leaders
• VentureRise - For CEOs with $5M+ in VC Raised

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SaasRise Hall of Fame

Congrats to the SaasRise members who have successfully exited or achieved a liquidity event for their company. View the Hall of Fame here.