Staff IT Systems Engineer, Thumbtack
AI and Automation
$152.2-231k
Salary dependent on location
Local services marketplace app
Be an early applicant
Local services marketplace app
1001+ employees
Be an early applicant
$152.2-231k
Salary dependent on location
1001+ employees
Company mission
Thumbtack's mission is to help homeowners care for their homes, all the way from minor retouching to fundamental remodelling projects.
Role
Who you are
- 5+ years of experience in IT systems engineering, infrastructure, or platform engineering in a distributed enterprise environment with a demonstrated track record of owning systems end-to-end, shaping technical direction, and driving cross-functional outcomes
- Deep, hands-on expertise designing and building automation and integration frameworks — Okta Workflows in production is required along with experience in tools like AWS Lambda, Workato, Jira Automations, Slack Workflows, or equivalent platforms
- Strong understanding of identity and access management systems and protocols (SAML, SCIM, OAuth2.0/OIDC, LDAP), with the ability to design scalable, secure IAM architectures across SaaS, cloud, and enterprise environments
- Applied AI and automation experience — a demonstrated track record of building AI-enabled workflows, agent-based patterns, or intelligent orchestration that reduces manual effort and improves system operations, not just familiarity with the concepts
- Scripting or programming fluency (Python, JavaScript, Shell, or equivalent) and working knowledge of AWS or other cloud platforms for building scalable, reliable automations and integrations
- Strong systems thinking, communication, and cross-functional influence — with the ability to navigate ambiguity, partner across teams, mentor others, and ensure security, compliance, and governance are embedded in every system you own
What the job involves
- As a Senior IT Systems Engineer on the IT Systems Architecture team, you’ll design and build the internal platforms, automation frameworks, and AI-enabled systems that power how Thumbtack employees work, including emerging patterns like agent-driven workflows and system orchestration
- This role goes beyond traditional systems administration — you will help evolve IT Infrastructure into a scalable, automation-driven platform that enables employees and teams to operate efficiently and securely
- You will play a key role in advancing automation and AI enablement across IT by integrating AI capabilities into workflows, building intelligent automations, and developing systems that reduce manual effort and improve how work gets done at scale
- You’ll partner closely with engineers, program managers, leaders, and cross-functional teams to deliver high-impact solutions across identity, SaaS platforms, cloud systems, and endpoint management
- A core part of this role is designing and building scalable automation and integration frameworks — leveraging tools such as Okta Workflows, APIs, and custom connectors to create event-driven workflows and enable self-service capabilities across internal systems
- You will help drive the convergence of automation and AI by identifying opportunities to streamline operations, connect systems more intelligently, and enable emerging patterns such as actions, orchestration, and system-driven workflows
- As a force multiplier, you’ll leverage your expertise in systems architecture, workflow automation, cloud services, authentication and access systems, and security to solve challenges across both day-to-day operations and longer-term strategic initiatives
- You are a strong technical leader and communicator with a passion for building scalable platforms, mentoring others, and delivering high-quality, forward-looking IT services
- Design and build AI-powered internal platforms and automation frameworks that connect systems, enable self-service, and scale IT capabilities — incorporating agent-based workflows, event-driven integrations, and intelligent orchestration across the infrastructure stack
- Own and evolve core IT systems (Okta, Google Workspace, Atlassian, Slack, Fleet, Linear, SentinelOne, Palo Alto Networks, AWS and more) as a cohesive, integrated platform — building automations and integrations that connect these systems rather than managing them in isolation
- Define and implement how AI and automation interact with internal infrastructure — including agentic workflows, system-to-system orchestration, and AI-enabled processes that reduce manual effort and improve how work gets done at scale
- Partner cross-functionally with engineers, leaders, and business teams to define systems architecture, automation strategy, and AI-enabled workflows — driving execution, influencing technical direction, and mentoring teammatesLead IT technical initiatives end-to-end — from design and stakeholder alignment through delivery and ongoing operations, along with managing vendor relationships, evaluating tools, and driving long-term architectural decisions
- Ensure security, compliance, and operational reliability across the infrastructure stack — including identity access controls, least-privilege design, system health monitoring, and scalable operational practices
Our take
ThumbTack is a local services marketplace app that pairs customers with skilled professionals. Instead of simply searching for a professional, users provide ThumbTack with details of the job they need completing and the professionals then pitch their services to the potential customer using credits. ThumbTack makes its money by charging the professional for these credits.
It positions itself as something a little different in a saturated local services space that is dominated by companies like Angie’s List, TaskRabbit, Yelp, eBay, and Amazon. It also focuses on a broad range of professionals, from traditional home services like electricians and painters to photographers, personal trainers, and birthday party magicians.
The COVID-19 pandemic saw a boost in business for ThumbTack as more people stayed at home and made changes to their properties, increasing the demand for home professionals. In fact, after 2019, the company doubled in value to $3.2 billion with its 2021 raise. Since its 2024 funding round, its updated app has 30 new features, and the company is partnering with the likes of trade-powering platform and Unicorn ServiceTitan, indicating Thumbtack's sustained sway in the market.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-5% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
Jun 2021
$275m
LATE VC
Jul 2019
$150m
SERIES F
Total funding: $699.4m
Company benefits
- Parental leave
- Health insurance
- Community matters | Sure, our ways of connecting have changed. But we haven’t missed a beat, from virtual concerts to “TTversary” celebrations to weekly catch-ups
- Always be improving | We bring out the best in our colleagues — and our product — by pushing each beyond what we believe we’re capable of. We give honest feedback, even when it’s hard
- Wellness is a way of life | We promote balance with generous PTO and company-wide holidays — and find our centers every Wellness Wednesday with yoga featuring a Thumbtack pro
- A worthy mission | In a world where tech is often seen as eroding good jobs, we’re helping small business owners thrive. Our product makes entrepreneurship accessible to everyone
- Driven by our values | Our values are the compass by which we make all our decisions. Each one matters: Lead with why, Make it count, Own it, Choose teamwork, and Say what you mean
- Plus, amazing benefits | All the benefits you’d expect, plus a few more: generous parental and fertility benefits, $1800 for Thumbtack services per year and a $1200 remote work stipend
- Virtual-first working model coupled with quarterly in-person events and Camp Thumbtack
- 20+ company-wide holidays including two week-long shutdowns
- Libraries (collaborative workspaces) in San Francisco, Salt Lake City, Toronto, and Manila
- Cell phone and WiFi reimbursements
- Subscriptions and Employee Assistance Program for mental health and well-being
Company HQ
SoMa, San Francisco, CA
Leadership
Marco Zappacosta
(Co-Founder & CEO)Having studied at Columbia University, Marco co-founded Thumbtack in August 2008. He has served as CEO since January 2009.
Jonathan Swanson
(Co-Founder & Chairman)Jonathan started his career creating financial market reports for the White House before co-founding Thumbtack in 2008. Currently Founder at Powerset and Athena.
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