Tackle (YC W21) - Time tracking on autopilot

From brand identity to AI-native product design, we provided the strategic execution and resilience needed to turn an ambitious vision into a $35K MRR reality.

From $5k to $35k MRR: Architecting product-led growth for a YC startup through pivots & persistence

CLIENT

Tackle AI

TIMELINE

2 Years

ROLES

Head of Product & Design

Website

www.timetackle.com

SERVICE PROVIDED

Tools

The Client & The Vision

Tackle(YC W21) began with an ambitious vision - to completely reinvent the calendaring landscape.

The founders, Syam Anupom (Our founder’s former colleagues from Disney) and Mika Sagindyk, envisioned an AI-powered platform that moved beyond simple time tracking to offer automated analytics, intelligent scheduling across time zones, and deep insights into how high-performing founders and executives spend their time.

The Core Challenge

The journey was a classic startup rollercoaster, requiring a designer who could be a chameleon.

The Only Designer: Dogpatch was the sole design partner supporting a team that grew to 6–8 engineers, owning and delivering every visual aspect of the company.
Constant Pivots & Scope Changes: The core vision—changing how people use calendars—proved to have a smaller market than anticipated. The team pivoted multiple times, including a major push into Hightime AI, an AI-Native Sales Workspace.
Navigating Market Reality: The challenge was balancing a grand vision with the need to find a niche, product-market fit, and revenue. Objectives and priorities could shift overnight.
Surviving External Shocks: After achieving a peak of $35k MRR with clients like Roblox, PwC, and the Chan Zuckerberg Initiative, the company was hit hard by the economic fallout from COVID-19 and the war in Ukraine, causing MRR to $5k-$7k MRR dramatically and forcing difficult downsizing.

Strategic Approach & Solution

Hasan embedded himself as a core strategic partner, not just a pixel-pusher.

Building the Foundation: Dogpatch Design established the entire product’s design language, creating the brand identity, marketing website, web application, and a Chrome extension that integrated directly into Google Calendar.
Deep Collaboration & “Whatever It Takes” Mentality: Dogpatch Design actively participated in product roadmap sessions, competitive research, and user interviews. The work included:
- Product Strategy: Helping prioritize features based on ROI and feasibility.
- UX Optimization: Redesigning the onboarding process and implementing a Product-Led Growth (PLG) flow with checklists to improve user activation.
- Hands-On Development: Writing front-end CSS for the Chrome extension to ensure pixel-perfect implementation when engineering resources were stretched.
The Hightime AI Pivot: During a key hack week, the team conceived and designed Hightime AI. Dogpatch Design led the design of futuristic, AI-enabled widgets, including one that researched meeting participants by pulling data from social media to generate personality insights and conversation tips for sales professionals—a feature far ahead of its time.

The Impact & Results

Tackle's story is one of resilience, learning, and tangible impact:

Revenue Growth: Under Dogpatch Design’s design leadership, Tackle grew from $5K to $35K in Monthly Recurring Revenue (MRR), validating product-market fit within a focused niche.
Strategic Pivots: The work on Hightime AI, though ultimately shelved, demonstrated the team’s ability to innovate rapidly and anticipate emerging market trends—particularly AI co-pilots—well before they became mainstream.
Survival Against Odds: Despite market shocks and a challenging total addressable market (TAM), Tackle endured where many others failed. Dogpatch Design built a stable, scalable design foundation that enabled the company to remain operational and default alive.
Enduring Partnership: Dogpatch Design’s long-term commitment is reflected in the continued advisory support provided years later highlighting a partnership built on trust, resilience, and shared execution, rather than a short-term transactional engagement.

Achievement

$ 0 K MRR

within 12 months.

0 %

Improvement in onboarding completion.

0 rd

Product Hunt Awards.

Key Takeaway

This case study showcases the reality of a startup designer's life: it’s not always about billion-dollar exits, but about endurance, adaptability, and doing whatever it takes to help the company survive, learn, and grow.

TimeTackle redefines productivity by transforming your calendar into an intelligent time-tracking command center. Our AI-powered platform seamlessly captures, categorizes, and analyzes activities right where work is scheduled – eliminating manual entry while delivering strategic insights.