Seth Sakamoto

Fractional CTO & CTO Advisor/Coach

With over 30 years of experience, I help founders, CEOs, CTOs, and other leaders level up their engineering and product functions across a wide range of industries, company stages, and challenges. I have led upgrades, turnarounds, and successful exits at companies such as Intuit, Constant Contact, Hipmunk, TuneIn, Envoy, TeamSnap, and many more.


As a Fractional CTO, I coach, diagnose, bridge gaps, and drive positive change using my extensive knowledge of building engineering and product in B2C, B…

Seth Sakamoto

Testimonials

  • Seth was an invaluable resource in guiding me as the engineering team at Stable grew. He ... helped me determine the right engineering processes to adopt at the right time, based on the size of the engineering team and scale of our product. He helped me navigate various people management issues and helped me develop robust strategies to balance urgent customer-facing issues with longer-term research projects as our product offerings were rapidly scaling up.

    Shantanu Sinha

    Shantanu Sinha

    Head of Engineering, Stable Auto
  • I’ve been working with Seth for 6-7 years now, allowing us to leverage is wide range of experience and knowledge. - Seth helped us in a Fractional VP of Engineering role, helping us diagnose several organizational pathologies early in our growth. - Seth has also worked as an advisor to me personally, helping me refine strategy, messaging, and prioritization. He brings a wealth of skills, and a pragmatic viewpoint from his years working a variety of startups. I’d recommend him unreservedly.

    Eric Ericson

    Eric Ericson

    Head of Engineering, Avail Car Sharing
  • Seth was a great choice during our transition between CTOs. He is practical, on the point, and cost conscious. Not all start-ups can afford a full-time CTO, and may prefer tentative solutions to address the initial business needs. Seth is the great person to help at the most difficult time of a start-up to reduce the unnecessary tech debt down in the road.

    Ning Zhang

    Ning Zhang

    Founder and CEO, Flatfee
  • Seth has helped us significantly improve the culture & quality of our engineering team over a short time period. ... He greatly accelerated the team's ability to work collaboratively and make velocity improvements. He was so good for engineering that we asked him to also help us with our product function, and he quickly made an impact there as well. Working with Seth has been one of the most valuable experiences for our company and me personally!

    Eric Yu

    Eric Yu

    Co-founder, Rutter
  • I've collaborated closely with Seth over the past year while leading and scaling an early-stage enterprise SaaS business as a first-time Founder. Seth's guidance, steeped in decades of hands-on expertise, has been instrumental in tackling various challenges I've encountered along the way. Moreover, his presence extends to our entire team, fostering an environment where each individual, myself included, can contribute their best work.

    Jamie Schiel

    Jamie Schiel

    CTO, Stable Auto

Work

Experience

  • Plato

    Plato

    Investor, Advisor, and Mentor

    Mar 2017 - Present

    Connecting engineering and product leaders with mentorship from experienced folks at companies beyond their immediate circles.

    • Company advisor and investor.
    • Helped hire Head of Engineering, shape executive team, and evolve product strategy.
  • Teamsnap

    Teamsnap

    Vice President of Engineering

    Jun 2020 - Apr 2022

    Series C B2B/B2C startup enabling amateur sports communication and coordination. Acquired by Waud Capital (private equity) in 2021. I was brought in to upgrade engineering.

    • Established direction via org and technology strategies, OKRs, unified roadmaps.
    • Established a strong, unified engineering culture through 6 Director/Sr Mgr hires, clear job expectations, operating mechanisms and forums, engineering tenets, and technology simplification initiatives.
    • Grew engineering from 18 to 47 over 12 months.
    • Built a globally distributed team via scaled-up hiring as well as using a nearshore partner, with 30% of the team working globally.
    • Doubled gender representation percentage while tripling the size of the team.
    • Improved team velocity and cycle time over 20% and achieved an enviable <2.5% regression rate.
    • Drove technology aspects of due diligence, buy and sell side.
    • Simplified technology stack/sprawl, reducing from 4 cloud hosting providers to 2 ($300k/yr efficiency gain), eliminating nearly 300 unused repos, and driving an architecture practice and platform roadmap.
  • Envoy

    Envoy

    Vice President Engineering

    Aug 2017 - Mar 2019

    Series B B2B/B2C startup focused on technology for physical offices. The flagship visitor registration product is seen in lobbies across the world. Brought in to grow the engineering team and culture. I also ran Product and HR temporarily and brought in a recruiting team.

    • Grew engineering from 18 to 52, distributed globally.
    • Rebuilt the mobile team, strengthened data team, and formed a production engineering team.
    • Kept regrettable attrition to 8% and increased diversity of the team from 5 to 15%.
    • Built a collaborative, learning, get-things-done, accountable culture via clear job expectations, hiring practice improvements, engineering principles, stronger tech leads, leadership coaching, KPIs/OKRs, and time investments in pairing and spiking.
    • Improved milestone hit rate from n/a (no milestones) to 80%+.
    • Upgraded the product development process, put strong people into positions of leadership, shelved low value tech projects in favor of higher value ones, and implemented visible accountability.
    • Moved from a monolith to microservices, and from Heroku to AWS, Lambda, Docker, and ECS.
    • Improved focus on flagship product while investing in new ones, culminating in the incubation and launch of 2 products over 12 months.
    • As our flagship product is in the security space, achieved compliance with security and privacy standards (SOC2, GDPR) and established programs to improve our security and system availability (99.9%+).
  • Tunein

    Tunein

    Vice President Engineering

    Apr 2016 - Sep 2017

    Series E consumer startup focused on audio streaming. Served over 70MM monthly active customers across mobile, web, and consumer electronics devices like the Amazon Echo. I was brought in to transform the engineering team into a world class one.

    • Established a technology direction that scaled and attracted talent. Evolved monolith and built microservices in Golang, went live with a new web stack built using React.js & Node.js, and relocated infrastructure to the cloud.
    • Transformed quality efforts from reactive to proactive. Brought open bug count down by 30% and bad bugs down to zero.
    • Grew the team by 55% from 45 to 75 motivated engineers and managers.
  • Hipmunk

    Hipmunk

    Vice President Engineering

    Dec 2013 - Apr 2016

    Popular YC-backed, series C consumer startup acquired by Concur in Oct 2016. Focus was on improving how people plan travel. We made it dead simple, intuitive, and fun! I led engineering and operations and even customer service.

    • Delivered software on par velocity-, quality-, and complexity-wise with competitors that were significantly larger. Achieved 70% code coverage and enabled engineers to safely canary-style deploy as often as 20x/day.
    • Established processes that taught best practices and amplified, not ate into, productivity.
    • Built operational capabilities from the ground up to world class. Formed devops team. Went from 96% systems uptime to 99.9% availability of systems and all key features. Established failover, monitoring and alerting, and eliminated pager fatigue.
    • Tackled gnarly software problems. High-volume search, data pipelines, NLP, relevance, performance, high scale, leading-edge UIs across web, mobile web, iOS, and Android. Adopted current technologies and built our own when appropriate.
    • Incubated and launched a brand new product - Hello Hipmunk, an AI-powered chatbot.
    • Grew engineering from 12 to 44 engineers, data scientists, and managers. Built an industry-recognized team with great execution and a strong culture.
  • Constant Contact

    Constant Contact

    Director of Engineering

    Jul 2012 - Aug 2013

    Publicly traded company building solutions for SMBs to grow their businesses

    • Grew and led a San Francisco engineering center. Built a startup culture, led move into a new office space, expanded San Francisco location to 20 in 10 months.
    • Led a team of 30 engineers and managers covering social media marketing apps and services.
    • Drove operational and cultural changes around continuous integration/continuous delivery, release engineering, distributed architecture & teams.
    • Evolved hiring practices & processes and led key architect and management hires across company.
    • Drove culture change in engineering. Upgraded code standards, devops behaviors, cultural norms, quality practices, engineering performance management, hiring, and office space.
  • Deem, Inc.

    Deem, Inc.

    Vice President Engineering

    Jul 2010 - Apr 2012

    B2B-focused ecommerce software company, providing white label platform for enterprises (internal use, loyalty programs). Hired to build out a relevance engine and became leader of the platform organization.

    • Grew from 28 -> 60 managers, engineers, and QA engineers.
    • Drove personalization, semantics, search, data feeds, payment and billing solutions, authentication, identity management, workflow, messaging/event systems, configuration management, configuration UI, and site infrastructure for the SaaS platform.
    • Implemented processes and tools to enable growth and scale, including agile/scrum, performance/scalability/project health dashboards, resource allocation decision tools, performance management.
    • Lowered MTTR and improved system performance and availability.
    • Led expansion into India including formation of 1st offshore engineering team.
    • Drove and contributed to M&A, including due diligence and integration of 2 acquisitions.
    • Drove increased performance of organization measured by project output, quality, talent improvement, and SLAs.
  • Intuit

    Intuit

    Director of Product Development

    Jun 2001 - Jun 2009

    • Led product development and technical operations for 1M+ customer / $400M+ Employee Management Services business targeting SMBs. Launched 15 products & features for payroll, direct debit, tax filing and payments, and employee benefits.
    • Directed organization of 130 managers, engineers, and partners located across US & India.
    • Acquired, grew, and motivated talented people … received world class performance management & job mobility scores, eliminated undesirable attrition (1 person over 3 years), built a track record of exporting talent from my organizations.
    • Drove the turnaround of our India development organization. In 1 year, turned a 7-person underperforming team into a 21-person high-performing team handling a core part of the business.
    • Led a 3 year decrease in defect rate with the same volume of product changes while reducing overall investment in core product.
    • Led technical operations improvements in shopping/entitlements platform over 6 months leading to a 3% increase (96->99%) in availability.
    • Drove adoption of open source, led offshore development strategy, evolved development processes (brought in Scrum), led change to increase investment in technical operations, and founded innovation program focused on creating new products/finding new sour
    • Built and leveraged technology partnerships with 3rd parties, drove co-development arrangements with other Intuit business units including joint efforts between the QuickBooks & TurboTax groups, and built close internal partnerships with product managemen

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