Let’s get started
By clicking ‘Next’, I agree to the Terms of Service
and Privacy Policy, and consent to receive emails from Rise
Jobs / Job page
QA Lead Software Engineer (Founding Role) image - Rise Careers
Job details

QA Lead Software Engineer (Founding Role)

About Chestnut

Chestnut, backed by a16z, is applying modern solutions to transform a $7B industry. Our customizable, easy-to-use producer management and compensation platform is purpose-built to address the insurance industry’s unique challenges.

We help customers break free from legacy constraints, static compensation models, and manual processes—turning commissions into a dynamic revenue driver that unlocks growth.

We’re tackling one of the hardest problems in insurance. If you love solving complex challenges and want to work directly with a founding team building something groundbreaking, let’s chat!

Job Description

We’re looking for a QA Lead Software Engineer to be our first QA hire and lay the foundation for quality engineering across the company.

This is a hands-on, high-impact role where you’ll define what QA looks like at Chestnut — from strategy to tooling to team growth. You’ll build our first test automation framework, champion quality across the stack, and play a key role in scaling our platform.

🔧 What You’ll Do

  • Build Chestnut’s QA strategy, tools, and processes from the ground up

  • Design and implement an automated test framework (we use Playwright + TypeScript)

  • Define what should be automated — and what shouldn’t

  • Work closely with engineering and product to integrate QA into our SDLC

  • Own quality metrics, test plans, and defect tracking

  • Set the stage for future QA team growth

🧠 What We’re Looking For

  • 5+ years in QA, including 2+ years in a lead or founding QA role

  • Strong with modern test frameworks (e.g., Playwright, Cypress, Selenium)

  • Proficient in scripting (TypeScript, Python) and familiar with CI/CD pipelines

  • Excellent communicator who can work cross-functionally and independently

  • Experience building automation frameworks or processes from scratch

✅ Bonus Points

  • Experience testing APIs and backend systems

  • Familiarity with cloud platforms (AWS, GCP, Azure)

  • Mobile testing experience

You’ll be joining a small, fast-moving team backed by top-tier investors (including a16z) and working on a product that’s transforming how insurance carriers operate.

Apply now to help define and lead QA at Chestnut.

Benefits

  • Competitive salary and equity, with 10 year exercise window for stock options

  • Remote-first work culture

  • Quarterly offsites for all of us to bond

  • Unlimited PTO with 4 weeks recommended per year

  • Top notch health, dental, and vision insurance subsidized by us

What You Should Know About QA Lead Software Engineer (Founding Role), Chestnut

Welcome to Chestnut, where we are on the cutting edge of transforming the insurance industry! We're excited to share that we're looking for a QA Lead Software Engineer to join our founding team. This isn't just any QA role; you'll be our first dedicated QA hire, laying the groundwork for quality engineering in an innovative environment. In this hands-on position, you’ll define what QA will look like at Chestnut, developing everything from our QA strategy to the necessary tooling and processes. Imagine being in the driver's seat as you build our initial test automation framework using Playwright and TypeScript, shaping our commitment to quality across our platform. You’ll collaborate closely with both engineering and product teams to seamlessly embed QA in our software development lifecycle (SDLC), ensuring that our systems are not just functional but exemplary. We’re searching for someone with at least 5 years of QA experience and a couple of years in a leadership role. If you've got strong expertise with modern test frameworks and a knack for scripting, you’ll fit right in! Plus, we value great communication skills as you’ll be working cross-functionally. If you also have experience with mobile testing or cloud platforms, that's a bonus. Join us at Chestnut to help redefine QA and work on a product that truly makes a difference. We're a remote-first team backed by top-tier investors, committed to your growth with competitive salaries and benefits like unlimited PTO. Let's innovate together!

Frequently Asked Questions (FAQs) for QA Lead Software Engineer (Founding Role) Role at Chestnut
What are the main responsibilities of the QA Lead Software Engineer at Chestnut?

As the QA Lead Software Engineer at Chestnut, your primary responsibilities will include defining and implementing the QA strategy, building an automated testing framework using Playwright and TypeScript, and working closely with engineering and product teams to integrate QA into the software development lifecycle. You'll also own quality metrics, develop test plans, manage defect tracking, and establish a foundation for future QA team expansion.

Join Rise to see the full answer
What qualifications are required to apply for the QA Lead Software Engineer position at Chestnut?

To qualify for the QA Lead Software Engineer position at Chestnut, candidates should have at least 5 years of experience in quality assurance, including 2 years in a lead or founding role. Proficiency with modern testing frameworks like Playwright, Cypress, or Selenium is crucial, along with experience in scripting with TypeScript or Python and familiarity with CI/CD pipelines.

Join Rise to see the full answer
What tools and technologies does the QA Lead Software Engineer at Chestnut use?

At Chestnut, the QA Lead Software Engineer will primarily use Playwright and TypeScript for building the automated testing framework. Familiarity with additional modern test frameworks, continuous integration and deployment (CI/CD) tools, and scripting languages such as Python will also be valuable in this role.

Join Rise to see the full answer
What type of work culture can a QA Lead Software Engineer expect at Chestnut?

Chestnut has a remote-first work culture that promotes flexibility and work-life balance. You'll be part of an ambitious and fast-moving team, and there’s a strong emphasis on collaboration and innovation, supported by competitive salaries and benefits such as unlimited PTO and quarterly team bonding offsites.

Join Rise to see the full answer
How does the QA Lead Software Engineer role contribute to Chestnut's mission?

The QA Lead Software Engineer plays a critical role in ensuring that Chestnut's product meets high standards of quality and reliability. By developing a robust QA strategy and automating testing processes, this position directly supports our mission to transform the insurance industry with cutting-edge technology, helping our customers break free from legacy constraints.

Join Rise to see the full answer
Common Interview Questions for QA Lead Software Engineer (Founding Role)
How do you define the role of QA in the software development lifecycle?

QA is essential in the software development lifecycle as it ensures that products meet the specified requirements and function correctly before deployment. As a QA Lead, you should emphasize the importance of integrating QA early in the process to catch defects sooner, define clear quality metrics, and maintain a continuous feedback loop between development and testing.

Join Rise to see the full answer
Can you describe your experience with automated testing frameworks?

In your response, detail specific frameworks you've worked with, such as Playwright or Selenium. Discuss how you’ve utilized these tools to build test automation frameworks, the challenges faced during the implementation, and how you achieved efficiency in testing processes through automation.

Join Rise to see the full answer
What techniques do you use to determine what should or should not be automated in testing?

When determining what to automate, consider factors such as test stability, repetitiveness, and complexity. High-impact, repetitive, and critical tests should be automated to save time and resources. Share examples from your experience where you made these decisions, explaining the criteria that helped shape your strategy.

Join Rise to see the full answer
How do you ensure quality and efficiency in your QA processes?

Discuss how you establish clear metrics and KPIs to ascertain the quality of your testing processes. Talk about your experience in creating test plans, defect tracking systems, and conducting regular reviews to identify improvement areas. Emphasize the importance of collaboration with cross-functional teams to achieve consistent quality.

Join Rise to see the full answer
Describe a time when you had to handle a major defect found during the test phase.

Provide a detailed scenario where a significant defect was discovered during testing. Explain how you identified the issue, the steps taken to reproduce it, and how you communicated this to the relevant teams. Highlight the corrective actions taken to resolve the defect and prevent similar issues in the future.

Join Rise to see the full answer
What role does communication play in QA leadership?

Communication is vital in QA leadership as it fosters collaboration, understanding, and transparency among teams. Discuss how you ensure that feedback and quality expectations are communicated clearly, both in written documentation and during discussions. Highlight the importance of being an advocate for quality across departments.

Join Rise to see the full answer
How do you stay updated with the latest trends in QA and testing?

Explain how you leverage various resources to stay informed about the latest QA trends, such as attending conferences, participating in webinars, engaging in communities, or following key industry leaders. Emphasize your commitment to continuous learning and adapting your QA practices accordingly.

Join Rise to see the full answer
What strategies do you have for building a high-performing QA team?

Discuss your approach to recruiting, training, and mentoring QA professionals. Emphasize the importance of fostering a positive work culture, setting clear expectations, providing growth opportunities, and promoting a sense of ownership and accountability within the team.

Join Rise to see the full answer
How would you approach scaling the QA processes as Chestnut grows?

Discuss your vision for scaling QA processes, including how you would document and standardize practices, enhance test automation, and onboard new team members. Highlight the importance of adaptability and how you'll adjust strategies as the company evolves.

Join Rise to see the full answer
What is a critical aspect of QA that you think is often overlooked?

One often-overlooked aspect of QA is the need for proactive test planning and early integration of QA in the development cycle. Explain how early involvement can significantly reduce defects and improve overall product quality, providing insights from your own experiences.

Join Rise to see the full answer
Similar Jobs
Photo of the Rise User
Posted 9 days ago

Join Humana as a Fraud and Waste Investigator to help combat healthcare fraud and enhance consumer experiences remotely.

Copeland Hybrid Lebanon, MO, USA
Posted 7 days ago

Join Copeland as a Quality Engineer, where you will play a vital role in enhancing quality processes in climate technology.

Photo of the Rise User

Become an integral player in food safety and quality assurance as a Quality Assurance Supervisor, overseeing lab operations and compliance.

Photo of the Rise User

Become a pivotal leader at CHEP as you ensure superior quality and drive continuous improvement initiatives in operations.

Photo of the Rise User
Posted 8 days ago

Join Nord Security as a QA Engineer where your skills will help shape internet privacy and security solutions for millions worldwide.

Photo of the Rise User
J.M. Huber Hybrid Shuqualak, MS
Posted 11 days ago

As a QA Manager at J.M. Huber Corporation, you'll lead quality assurance efforts in a global manufacturing environment.

Photo of the Rise User
Posted 10 days ago
Inclusive & Diverse
Rise from Within
Mission Driven
Diversity of Opinions
Work/Life Harmony

Citi is seeking a Senior Developer in Test to lead QA automation efforts for an FX trading platform in London.

Photo of the Rise User

Join our team as a Mobile App Tester to enhance our recruitment services with your testing expertise in BLE technology.

Photo of the Rise User
Inclusive & Diverse
Rise from Within
Mission Driven
Diversity of Opinions
Work/Life Harmony
Transparent & Candid
Growth & Learning
Fast-Paced
Collaboration over Competition
Take Risks
Friends Outside of Work
Passion for Exploration
Customer-Centric
Reward & Recognition
Feedback Forward
Rapid Growth
Medical Insurance
Paid Time-Off
Maternity Leave
Mental Health Resources
Equity
Paternity Leave
Fully Distributed
Flex-Friendly
Some Meals Provided
Snacks
Social Gatherings
Pet Friendly
Company Retreats
Dental Insurance
Life insurance
Health Savings Account (HSA)
Photo of the Rise User
Inclusive & Diverse
Rise from Within
Mission Driven
Diversity of Opinions
Work/Life Harmony
Transparent & Candid
Growth & Learning
Fast-Paced
Collaboration over Competition
Take Risks
Friends Outside of Work
Passion for Exploration
Customer-Centric
Reward & Recognition
Feedback Forward
Rapid Growth
Medical Insurance
Paid Time-Off
Maternity Leave
Mental Health Resources
Equity
Paternity Leave
Fully Distributed
Flex-Friendly
Some Meals Provided
Snacks
Social Gatherings
Pet Friendly
Company Retreats
Dental Insurance
Life insurance
Health Savings Account (HSA)
MATCH
Calculating your matching score...
FUNDING
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, remote
DATE POSTED
April 22, 2025

Subscribe to Rise newsletter

Risa star 🔮 Hi, I'm Risa! Your AI
Career Copilot
Want to see a list of jobs tailored to
you, just ask me below!
LATEST ACTIVITY
Photo of the Rise User
12 people applied to QA Analyst II at Super.com
Photo of the Rise User
7 people applied to QA Tester at Datadog
o
Someone from OH, Cincinnati just viewed Marketing and Communications Consultant at osu
W
8 people applied to QA Engineer at WhiteTech
Photo of the Rise User
Someone from OH, Toledo just viewed Registered Nurse (Part-time) at Calibrate
Photo of the Rise User
Someone from OH, Toledo just viewed Clinical Research Associate II at Alimentiv
Photo of the Rise User
Someone from OH, Cleveland just viewed IT Support Engineer at Level AI
Photo of the Rise User
Someone from OH, Dayton just viewed Customer Content Specialist at Cision
Photo of the Rise User
Someone from OH, Cuyahoga Falls just viewed Senior Corporate Communications Manager at Bumble Inc.
Z
6 people applied to Jr/Mid QA Engineer at Zipdev
Photo of the Rise User
Someone from OH, Cincinnati just viewed Senior Financial Analyst at Workday
Photo of the Rise User
Someone from OH, Cincinnati just viewed Financial Planning and Analysis Lead at JLL
Photo of the Rise User
Someone from OH, Cincinnati just viewed Senior Financial Analyst at American Express
Photo of the Rise User
Someone from OH, Cincinnati just viewed Senior Analyst, Operations at American Express
Photo of the Rise User
Someone from OH, Cincinnati just viewed Strategic Finance Analyst, Corporate at Benchling
Photo of the Rise User
Someone from OH, Cincinnati just viewed Senior Analyst, Project Finance at Apex Clean Energy
Photo of the Rise User
Someone from OH, Cincinnati just viewed Senior FP&A Analyst, Sales at GitLab
Photo of the Rise User
Someone from OH, Cincinnati just viewed FP&A Analyst at Lithic
Photo of the Rise User
13 people applied to Video Game Tester - FQA at Side