Building for Founders: What We Learned from 100+ Beta Users

Key Takeaways

• Our 100+ beta users were mostly seed-to-Series A SaaS founders, agency leaders, and solo startup builders across the US.
• Founders needed ultra-fast, command-style workflows—automation that saved them from “tool overload.”
• The top five use cases included task automation, multi-channel messaging, analytics summarization, calendar syncing, and client onboarding.
• Creative, unexpected applications included automated investor updates and “AI partner” brainstorming.
• The #1 feature request was a “single unified conversation” with context-aware smart commands.
• Usage peaked between 7-9am and 8-10pm, hinting at the real founder hustle work hours.
• Founder workflows are scrappier, require more flexibility, and demand less hierarchy than enterprise tools.
• Beta feedback led us to prioritize fewer features—but deeper integration and speed.
• Founders want tools that eliminate, not just “manage,” busywork.
• Final lesson: Building founder-focused tools requires building with founders, not for them.

Why Founders Need Different Tools

If you’re a founder, you know the pain: a calendar packed past midnight, Slack blowing up, Stripe pings in one tab and client questions in another.

The average US founder now manages 8-12 apps just to track basic business operations. Tool overload isn’t a small inconvenience—it’s a productivity killer.

When we set out to build SimpleDirect Chat, we knew “productivity” for founders wasn’t the same as it was for big enterprise teams.

We launched a closed beta in late 2024—inviting over 100 early-stage founders to break our tools, push our limits, and show us what actually works.

Here’s what we learned. And how you’ll benefit from it.

Beta Program Overview: How We Recruited and Managed Our Beta Cohort

Recruitment:
Our priority? Real US founders, ideally at the 0-50 employee stage. We sourced via:

• YC and On Deck founder communities
• Twitter DMs and targeted LinkedIn posts
• Referrals from existing SimpleDirect contractor users

Management:

• Each beta user got a private onboarding and a direct Slack/Discord channel to our team.
• Weekly office hours and monthly feedback calls
• Anonymous usage tracking (with consent) for deep product insights
• Feedback rewards (free months, swag)

Results?
109 founders joined from 12 US states, with a near 64/36 split between SaaS tech teams and digital agency/consultancy leaders.

User Demographics: Who Our Beta Founders Were

Out of 109 participants:

• 71% SaaS founders (pre-seed to Series A)
• 22% modern agency owners (digital marketing, creative, consultants)
• 7% technical freelancers (ex-FAANG/BigTech contractors, product managers)

Location:

• Bay Area, Austin, NYC, Denver, Atlanta & remote hubs
• 22% were fully distributed teams
  Average company age: 1.7 years
  Median team size: 8 employees

Top 5 Use Cases: How Founders Used SimpleDirect Chat

Here’s what founders really did with SimpleDirect Chat, by the numbers:

• Task Automation & Delegation (94%): Automating “remind me,” “send this to Slack,” and “update Asana” commands.
• Multi-Channel Client Messaging (83%): Unified email, SMS, and in-app messaging, especially for agencies.
• Analytics/Finance Summarization (65%)

• “Summarize Stripe revenue for this month.”
• “Show churn last quarter.”

• Calendar and Meeting Sync (61%)

• “Reschedule my Thursday calls.”
• “Block focus time 2-4pm.”

• Client Onboarding and Support (59%): Generate onboarding docs, automated client check-ins, AI support chat.

Unexpected Applications: Creative Uses We Never Saw Coming

Founders always break the rules—in the best way. Here’s how they surprised us:

• Automated Investor Updates
  One founder hooked up SimpleDirect to ping monthly progress snapshots straight to their investor list—zero manual compiling.
• “AI Partner” Brainstorming
  Another added a weekly Friday morning prompt: “Ask me 3 tough questions about my roadmap.”
• Job Candidate Coordination
  Automated texting scheduling links to interview candidates, piping replies right into Chat.
• Quick Legal Review
  Feeding NDAs and founder agreements for “summarize risk” commands.

These weren’t in our playbook—but we quickly made them easier.

Feature Request Deep Dive: What Founders Really Wanted

We tracked 182 unique feature asks over three months. Here’s what stood out:

• #1: Unified Conversation Thread
  Founders wanted everything—emails, support tickets, tasks, docs—grouped by client or project, not by app.
• #2: Contextual Smart Commands
  “If I type ‘send onboarding docs to new lead,’ it should figure out the CRM, not make me pick.”
• #3: Faster, Deeper Integrations
  Speed and reliability with Slack, Gmail, Stripe, Notion, and Calendar were must-haves.
• #4: Fewer Clicks, More Keyboard
  Founders abhor modal popups and slow load times. They want fast, keyboard-first commands.

How did we respond? Our 2025 build freezes new features, instead deepening integrations, boosting speed, and simplifying the UI.

Usage Patterns: When, How, and What Founders Automated

• Peak usage times:
  • 7:00–9:00am (pre-team standup)
  • 8:30–10:30pm (“catch up” hours)
• Session length:
  • Median: 12 minutes
  • 1 in 4 sessions lasted under 3 minutes—founders dip in for quick, decisive actions.
• Most used document types:
  • Investor/pitch decks (PDF/Google Slides)
  • Stripe exports
  • Meeting notes (Google Docs)

Key Insight:
Founders automate “bursts” of work between context switches—not long, linear workflows.

Success Stories: Real Productivity Gains

Case Study: Samantha, Seed-Stage SaaS Founder (Denver, CO)

• Saved 8 hours/week automating client onboarding via Chat
• 2X faster meeting scheduling with Command + Meet integration
• $3,200 saved monthly by eliminating three SaaS subscriptions

Case Study: Leo, Digital Agency Owner (Austin, TX)

• Used voice-to-text plus Chat to manage client check-ins during commutes
• Achieved 35% decrease in time spent on routine reporting

Challenges & Solutions: What Didn’t Go as Planned

• Integration Headaches:
  Early friction with Gmail and Slack APIs frustrated power users.
  Solution: Added direct OAuth, better error prompts, and quick reconnect tools.
• Over-automation:
  Some founders set up complex rules—then couldn’t remember them.
  Solution: Visual workflow mapping and a “dry run” preview.
• Mobile experience lacking:
  Several testers needed mobile-first, not desktop-first, UX.
  Solution: Launched mobile-optimized web app in 2025.

How the Beta Shaped SimpleDirect: Major Product Evolutions

• Consolidated features around chat/command workflows—fewer tabs, more context.
• Deepened integrations with Google, Slack, Stripe, and calendar apps.
• Faster, global search—across all data sources, not just SimpleDirect.
• Focus on real-time feedback—every command explained, every error visible.

And—we tripled our QA coverage for SaaS-first workflows.

Founder Insights: How Founder Needs Differ from Enterprise

What we learned:

• Founders crave elimination, not just “optimization” of work.
• Flexibility > rigidity: Founders want to hack, not follow best-practice playbooks.
• Documentation matters less than context: “Just show me what’s due and who’s waiting.”
• Keyboard shortcuts and command palettes beat wizards and onboarding flows.
• Real-time, human support outperforms “knowledge bases.”

Bottom line:
Building for founders means speed, simplicity, “tinkerability”—and a short path from problem to action.

Conclusion: Building Tools for the Makers, Not the Managers

Over 100 founders helped us stress-test SimpleDirect Chat. They showed us the edges of productivity tools—and how “founder work” is different than enterprise process. The final product wasn’t what we imagined, but what they pushed us toward: Fast. Thin. Unified. Flexible.

If you’re a founder drowning in context switches, we built SimpleDirect with (and for) you. Dive in, tell us what breaks, and help us keep building for builders.

Newsletter Blurb:

100+ beta users taught us these 5 things about founder tools:

1. Founders need command-driven, context-rich workflows (not dashboards).
2. Automations must eliminate—not just manage—busywork.
3. Keyboard shortcuts beat popups, every time.
4. Unified conversations matter more than “features.”
5. Beta feedback is gold—tools should evolve with real users, not spreadsheets.

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