The 7 most evil GTM tactics for B2B SaaS

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Welcome back to issue #20 of the Zero to $10M ARR Newsletter.

Here's what we have on the docket for today:

• Helply's Vitals: The rundown of our make-or-break metrics from Nov 6th - Nov 13th.
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• Weekly Beats: Here we recap Helply's most important "A Ha" moments and "Oh Sh*t" challenges from the last week on Our Journey to $10M ARR.
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• Weekly Deep Dive: Today I'm breaking down the 7 most evil GTM tactics for B2B SaaS and how to use them. Think of this as a crash course on how to think like a supervillain for founders who are feeling a little subversive and looking for their unfair advantage.
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• Alex & Tom Show Ep. 6: In this 6th episode of the Alex and Tom show, we show you what it means to be in FOUNDER MODE with a look at a 'day in the life of Alex' (founder of GrooveHQ and Helply).

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Helply's Weekly Vitals

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Every week, I'm laying out the do-or-die numbers for Helply–these are what I consider the make-or-break metrics for a B2B SaaS company.

As we evolve through the stages of a B2B SaaS lifecycle, so will the metrics. These are the numbers I obsess over as we push Helply to the next level.

Where we are:

🎯Development and MVP Stage

Goal: Build and validate the Minimum Viable Product (MVP). For this stage, our goal is to book 100 Helply demos and generate 35 pre-sales of Helply.

Focus: Testing the MVP with early adopters, gathering feedback, and iterating using a sales-led motion via live demos.

Current Stats:

💡Insights:

Want to dive into Helply's entire growth dashboard? You'll see every metric we're tracking as we fight our way through each stage of the B2B SaaS lifecycle. If you want to know what really goes on under the hood of a SaaS startup, this is your all-access pass. Take Me There!

Helply's Weekly Beats

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Here's the recap of Helply's most important "A Ha" moments and "Oh Sh*t" challenges from the last week. In the spirit of full transparency, every week we pull back the curtain on everything we do and leave no stone unturned.

👉 Follow along as we grow from $0 to $10M ARR in real-time via our Journey Page.

November 5th, 2024

Cold Outreach & Amazon Gift Cards? Why not…

Instead of selling, we're asking for feedback and offering a $100 Amazon card.

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Day one results? Night and day difference. We're getting responses from exactly the kind of SaaS companies we want to talk to.

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It's funny how asking for help instead of pushing a sale changes things.

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Let's see if this feedback-first approach has legs.

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November 8th, 2024

Our First Fleet Goes Live

Milestone hit. Seven companies actively using Helply in the wild. We're still pre-revenue, but the rubber has met the road.

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Each of these companies is stress-testing our AI in real support scenarios. It's like watching your kid take their first steps – nerve-wracking but exciting as hell.

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No amount of customer interviews or market research can replace seeing your product solve real problems in real time. Now we watch, learn, and iterate based on actual usage.

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Game on.

Weekly Deep Dive

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The 4 most evil GTM tactics for B2B SaaS.

How to think like a supervillain for founders who are feeling a little subversive and looking for their unfair advantage.

Alistair Croll (Author of Lean Analytics) was a recent guest on Lenny’s Podcast.

They spoke about the most subversive growth and GTM tactics deployed by successful companies.

This got me thinking.

If I wanted to approach B2B SaaS GTM like a supervillain what would I do?

Here’s my list of the 4 most subversive GTM tactics that are just evil enough to work (while still being ethical).

1. The “Search & Destroy” Lead Generation

Weaponize Competitor Review Sites

Real-World Example: Gong vs Traditional Sales Tools

• Created scripts to monitor G2/Capterra
• Identified frustrated customers of competitors
• Automated outreach within hours of negative reviews
• Offered “rescue package” with migration support
• Result: 40%+ conversion on these leads

Tactical Deployment

1. Set up monitoring for competitor review sites
2. Create custom outreach templates by pain point
3. Build migration calculator showing 3-year savings
4. Offer free migration + onboarding for switchers
5. Time outreach to renewal windows
6. The “Forced Virality” Engine

2. Weaponize Your Free Users

Real-World Example: Loom vs Screen Recording

• Made sharing create free user accounts
• Forced video viewers to sign up
• Targeted enterprise domains
• Used viewer data to map org structures
• Result: Each free user generated 3.5 new users

Tactical Deployment

1. Make content sharing require account creation
2. Track corporate domain signups
3. Map organizational hierarchy through usage
4. Target departments with multiple free users
5. Use internal champions for expansion
6. The “Pipeline Poisoning” Campaign

3. Sabotage Competitor Sales Cycles

Real-World Example: Close.io Early Days

• Created comparison pages for every competitor
• Optimized for “[Competitor] Alternative” keywords
• Targeted customers in active buying cycles
• Inserted doubt into competitor processes
• Result: Intercepted 30% of competitor deals

Tactical Deployment

1. Build SEO-optimized comparison pages
2. Create FUD content about competitor weaknesses
3. Run targeted ads during buying season
4. Offer “buyer’s guide” that favors your features
5. Make competitor evaluation criteria favor you
6. The “Dark Funnel” Strategy

4. Build Pipeline Before They Know They’re Looking

Real-World Example: Drift, a Salesloft company vs Live Chat

• Built free email tracking tool
• Identified companies researching solutions
• Reached out before formal buying process
• Shaped requirements before competitors knew
• Result: Won 60% of deals they detected early

Tactical Deployment

1. Create free tools that detect buying intent
2. Monitor tech stack changes in target accounts
3. Track content consumption patterns
4. Reach out during research phase
5. Shape RFP requirements early

5. The "Trojan Horse" Integration Play Weaponize Your Integration Access

Real-World Example: DocuSign vs Established eSign

• Built deep Salesforce AppExchange integration
• Collected usage patterns of legacy solutions
• Identified accounts with low adoption rates
• Targeted orgs during contract renewals
• Result: Captured 70% of enterprise switching

Tactical Deployment:

1. Create native integrations with market leaders
2. Monitor usage patterns and friction points
3. Build migration tools for competitor data
4. Target accounts showing adoption issues
5. Time expansion with renewal windows
6. The "Shadow IT" Land & Expand Weaponize Individual Users' Pain Real-World Example: Slack vs Enterprise Chat

6. The "Shadow IT" Land & Expand Weaponize Individual Users' Pain Real-World Example: Slack vs Enterprise Chat

• Targeted individual team leads, bypassed IT
• Made free tier irresistibly useful
• Spread through team collaboration features
• Created organizational dependency
• Result: 3x faster enterprise penetration

Tactical Deployment:

1. Build consumer-grade UX for business tools
2. Enable viral team collaboration
3. Create workflows too valuable to remove
4. Drive adoption before IT discovery
5. Present enterprise features when challenged
6. The "Ecosystem Arbitrage" Strategy Weaponize Platform Dependencies Real-World Example: PagerDuty vs Legacy Alerting

7. The "Ecosystem Arbitrage" Strategy Weaponize Platform Dependencies

Real-World Example: PagerDuty vs Legacy Alerting

• Monitored ServiceNow marketplace pricing
• Built superior alerting at 50% lower cost
• Targeted during marketplace renewals
• Offered seamless migration tools
• Result: 45% conversion of targeted accounts

Tactical Deployment:

1. Map competitor pricing in marketplaces
2. Build focused feature parity
3. Create dramatic cost savings calculator
4. Time outreach to renewal windows
5. Provide white-glove switching support

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Alex and Tom Show Ep.6

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In this sixth episode of the Alex and Tom show, we talk about what it really means to be in founder mode--diving deep into the daily responsibilities and challenges of running both Groove and Helply simultaneously.

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1. Customer Engagement:

• Conducted 350+ customer development calls
• Actively participates in demos and onboarding
• Shadows all sales demos, even when not leading
• Maintains direct involvement in customer support
• Uses every interaction to inform product decisions

2. Product Development:

• Designs all UX/UI in Figma personally
• Acts as primary product manager
• Conducts daily QA and feature reviews
• Prioritizes features based on customer feedback
• Works directly with development team

3. Marketing and Messaging:

• Writes daily LinkedIn content
• Creates and refines core messaging
• Reviews all outbound strategy
• Crafts value story outlines
• Develops unique selling propositions

4. Go-to-Market:

• Uses bullseye framework for channel selection
• Balances inbound and outbound efforts
• Plans comprehensive 2025 GTM approach
• Evaluates multiple marketing channels
• Tests new growth experiments

5. Team and Operations:

• Runs weekly L10 meetings
• Conducts focused development check-ins
• Minimizes unnecessary meetings
• Maintains productivity focus
• Guides team communication

6. Vision and Culture Building:

• Creates and iterates on VTO (Vision Traction Organizer)
• Establishes core company values
• Aligns team with company vision
• Guides differentiation strategy
• Builds company culture from ground up

7. Financials:

• Reviews weekly P&L statements
• Plans budget allocation
• Projects revenue forecasts
• Manages startup expenses
• Plans path to $1M ARR

Alright, that does it for issue #20 of the Zero to $10M ARR Newsletter!

Let us know what you thoughts by leaving a comment on today’s LinkedIn post.

See you next week!

Alex

P.S. Interested to see how Helply can reduce support costs and get your users the answers they want, quickly and accurately (24/7)?

• Visit helply.com​
• Request a demo
• We'll set you up with a FREE account to trial the software -- and hold you hand as we help you implement the whole thing

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