Amitav Chakravartty

Co-Founder

San Francisco, California, United States28 yrs 1 mo experience
Most Likely To Switch

Key Highlights

  • Built and exited multiple companies with $10M+ ARR.
  • Expert in scaling SaaS and PropTech ventures.
  • Angel investor supporting early-stage AI startups.
Stackforce AI infers this person is a SaaS and PropTech expert with a strong focus on AI-driven solutions.

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Skills

Other Skills

Cross-functional Team LeadershipStakeholder ManagementApache KafkaData ScienceC++Web ServicesAgile MethodologiesSoftware Project ManagementQuality AssuranceRequirements AnalysisWeb DevelopmentOpen SourceAJAXEnterprise SoftwareTechnical Leadership

About

I’m a repeat founder and YC alum (W13) with a track record of building, scaling, and exiting companies in SaaS and PropTech. Across multiple ventures, I’ve taken products from concept to $10M+ ARR with an exit, led high-performing engineering and product teams, and delivered scalable systems that have supported millions of users. As a founder, I specialize in navigating the earliest stages and turning ambiguity into clarity, customer pain into product insight, and early traction into durable growth. I’ve built platforms from the ground up, created new revenue lines, and consistently aligned technical execution with business outcomes. My experience spans growth, payments, AI/ML, infrastructure, and enterprise integrations, with a focus on delivering measurable impact rather than incremental features. After exiting my previous startup, I’ve continued operating as a technical and strategic leader building teams, mentoring CTOs, and advising founders on GTM, product strategy, and fundraise readiness. As an angel investor, I back early-stage founders solving real operational problems with AI and automation, drawing on my experience scaling product and engineering orgs. At heart, I’m an engineer and builder. I write code, prototype fast, and obsess over customer discovery. I thrive in environments where speed, ownership, and discipline matter and where the goal is not just to ship, but to create something that outperforms incumbents by an order of magnitude. If you’re building in SaaS, PropTech, or AI-driven workflows and want to discuss product, GTM, or fundraising strategy, feel free to reach out: amitavc at gmail dot com.

Experience

Stealth

Building New

Nov 2025Present · 5 mos

Self employed

Consultant & Advisor

Jan 2023Aug 2025 · 2 yrs 7 mos · San Francisco Bay Area

  • Assisted founders in integrating AI into their product roadmap.
  • Helped to build Applied AI features
  • Advise and work with the team on 0-1 product journeys
  • Advised CTOs on overcoming engineering challenges.
  • Mentored engineering leaders to enhance their skills and leadership abilities.

Cohesity

Director Of Engineering - Marketplace & Apps Platform

Jul 2022Jan 2023 · 6 mos · San Francisco Bay Area

  • As Director of Engineering for the Marketplace & Apps Platform team at Cohesity, I led a new portfolio business to drive revenue generation through the development of apps designed to run on managed Kubernetes (K8) at scale for on-premise and in the Cloud built on top of Cohesity's data backup clusters. Lead the innovation vertical, marketplace ecosystem for b2b providers, ensuring that it remains competitive, secure, and scalable.

Splice

2 roles

Director of Engineering - Growth & Monetization

Promoted

Jan 2021Jul 2022 · 1 yr 6 mos · Remote

  • Responsible for multiple teams at Splice which manage the Customer Journey, Identity, and Monetization. My team is responsible for engagement and improving the number of subscribers. The payment team maintains the core set of revenue-generating systems like payment infrastructure, subscription, and identity across the Platform. Build payment & growth tech Portfolio to impact immediate revenue. Splice is a rapidly growing platform similar to SoundCloud, offering a wide range of sounds to music producers.

Director of Engineering - Monetization

Jul 2020Jan 2021 · 6 mos · Remote

  • Led the monetization, API, and managed the payment infrastructure. Payment connected to Stripe, PayPal, and International providers.

Angel investor

Angel Investor

Nov 2019Present · 6 yrs 5 mos

  • Invested in over 30 startups, both from Y Combinator and other sources, across various stages.
  • Empowered founders with ambitious visions, supporting their journey from concept to execution.
  • Developed a keen understanding of startup ecosystems and the challenges faced by early-stage companies.

Housecanary

Engineering - Investor Suites(Real Estate)

Feb 2019Jul 2020 · 1 yr 5 mos · San Francisco Bay Area

  • Led the engineering teams in developing a new marketplace tailored for real estate investors, addressing a $7.4 trillion market in the United States.

Y combinator

Advisor - Startup School

Jul 2018Jul 2019 · 1 yr · San Francisco Bay Area

  • Advised early founders on idea execution, revenue generation, and resource preparation at Y Combinator.
  • Equipped startups with tools for present and future success.
  • Facilitated growth and innovation within the startup community.
  • Fostered a culture of learning and collaboration among budding entrepreneurs.

Redawning.com

2 roles

Vice President, Software Engineering - PMS Integration

Feb 2017Feb 2019 · 2 yrs

  • VaycayHero was acquired by RedAwning in 2017 to strengthen its technical capabilities and improve customer retention.Helped to build the Tech and Operations team for the Travel Platform. Care a lot about creating human workplaces and scalable, sustainable processes, and culture. I defined our engineering values, sponsored hackathons, and deputized working groups to establish guidelines for technology selection, architecture review, documentation, and monitoring.
  • Some highlights:
  • Architected a high-performance strategic roadmap enabling rapid 3X projected growth which leads to $40M series A
  • Led the seamless integration of RedAwning and VaycayHero platforms. Harmonized Python/Node/Java stacks, oversaw 400+ client integrations, built processes to improve maturity, and created a scalable support structure.
  • Turn around a dysfunction team to a performing team. Post-acquisition, transformed the existing dysfunction team to a performing team using agile metrics and best practices. Built the organizational chart with goals, career ladder with clear responsibilities, and KPI
  • Build additional Property management Integrations so the reach of the property managers increase by 10X
  • Managed 6 large teams of 45 people constitutes of engineers, operations, and data scientists, architects, managers, directors.
  • Hired, and mentored growth engineering, data analytics, and operations team from the ground up and prepared the team to achieve the next milestone.

Vice President Of Software Engineering

Feb 2017Oct 2017 · 8 mos

Vaycayhero

Chief Technology Officer, Co-Founder

Jan 2013Apr 2017 · 4 yrs 3 mos · San Francisco Bay Area

  • VaycayHero (Y Combinator W13) is a platform for aggregating professionally managed vacation rentals. VaycayHero operates a B2C/B2B channel distribution platform that distributes its inventory OTA. Scaled services over a microservices architecture. Assisted in scaling the company from 0 to 45 people. VaycayHero is backed by YCombinator, an all-star list of VCs, and raised around $5M.
  • VaycayHero.com acquired in March’2017 by RedAwning.
  • Some highlights:
  • I was responsible for all aspects of Technology, Product Management, and Operations to build $10M+ ARR and building a network of 500+ suppliers representing 43K+ vacation rentals, at less than $2 acquisition cost per rental.
  • Grown the engineering team from 0-15 within 2 years, motivated the team to build a travel tech platform.
  • Grown as fast as we can to keep pace with rapid business growth without compromising the collaborative, inclusive culture of ownership that makes us unique.
  • Hired each of the team members carefully to build a team of diversity, fun-loving, and with great work ethics.
  • Accelerated operational maturity, product planning, and product development cycles.
  • Lead early-stage adoption of AWS technology moved successfully from monolithic to a microservice architecture to scale the platform with increasing API transaction volume 90M/month.
  • Built the technical foundation for dynamic pricing algorithms, predictive pricing model, and search optimization using a large dataset
  • Implemented 300+ growth hack ideas to grow the customers
  • My philosophy is to culture over process, coaching over telling, cooperation over competition, data over opinion, communication over the direction. As a technical head, I tried to model these behaviors every day and to develop technical leaders with diverse toolkits and good judgment. These helped us to build leaders at every level and able to generate millions of revenue with a small team.

Shopnics

Co-Founder

Oct 2008Oct 2009 · 1 yr

  • Shopnics.com is a product comparison shopping engine aiming to help users easily find products based on their needs. Shopnics helps user’s to make an informed decision based on product attributes. Shopnics AI Engine rates products based on their specification and user needs and then plots them on a visual graph where users can compare multiple products easily.
  • Some highlights:
  • Launch the product within 6 months.
  • Raised seed money of $50k
  • Build the team from 0-3 people

Serena software

2 roles

Chief Architect - SaaS

Promoted

Oct 2007Jan 2013 · 5 yrs 3 mos

  • Chief Architect, developed the SaaS version of their BPM software. Established a system architecture strategy to support the technical strategy and next generation of products on the SaaS platform.
  • Some highlights:
  • Responsible to launch their BPM software in the Cloud as “Cloud-First” architectures.
  • Delivered multiple in-build business process solutions for clients from B2B/B2C, supply chain, finance, and CRM, education, other government agencies.
  • I have written multiple white papers on scalability and security and presented at conferences and
  • they referred by various journals published under the International Journal of Advanced Computing.
  • I have scaled the SaaS product for 1M active users which generated $100M ARR.
  • I have come up with the scalable deployment architecture which is pre-AWS
  • I have designed and architected the Client Provision component so that new customers get a quick experience within 5 minutes of onboarding.
  • Tracked multiple metrics to understand better adoption of the SaaS offerings
  • Helped on Goto Market strategies

Staff Engineer

Jan 2007Jan 2008 · 1 yr

Tavant technologies inc

3 roles

Engineering Manager

Jan 2003Jan 2005 · 2 yrs

Senior Software Development Manager - Loan Origination System

Promoted

Aug 2002Oct 2007 · 5 yrs 2 mos

  • Responsible for all aspects of core software development and architecture of a SOA based financial Systems.
  • Some highlights:
  • Managed multiple teams to build an SOA based Financial Systems for a Mortgage Company.
  • Coached, developed, and promoted several leaders into key roles in the technology industry.
  • Hired and built a team of onshore and offshore engineers to architect next-generation SOA based financial software.
  • This platform helped customers for significant savings in operational costs and streamline the process.
  • Published papers in JavaOne 2007, Ajax World 2007

Development Team Lead

Jan 2002Jan 2003 · 1 yr

Tarang software technologies

Technical Lead

Mar 2000Jul 2002 · 2 yrs 4 mos · India

Dharma systems

Software Engineer

Jan 1999Mar 2000 · 1 yr 2 mos

Reliance

Assistant Manager

Mar 1998Feb 1999 · 11 mos · Greater Rajkot Area

  • Responsible for designing of Port and Jetty

Education

Y Combinator

Enterprenurship — Entrepreneurship

Jan 2012Jan 2013

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