Director Of Engineering

We are seeking a Director of Engineering (E-commerce) for a remote, full-time, and direct hire role for one of our amazing partners.
You will lead the development and enhancement of their customer-facing applications (web and mobile), e-commerce store, and customer service back-office systems. This role will be pivotal in shaping their product strategy and will directly impact the success of this high-scale ecommerce platform. We are looking for a data-driven problem solver that strives for impact, scalability, and simplicity. You should be a natural leader in the eCommerce space, with a proven track record of building high-performing teams and driving impactful results.
Responsibilities:

You will drive performance optimization initiatives across both web and mobile platforms to ensure fast and responsive applications, and result in increased user satisfaction and engagement with the platforms.
You will provide technical leadership and strategic direction for the development of all customer-facing applications and ensure alignment with overall business goals and objectives. This includes web and mobile platforms, e-commerce store, and customer service tools.
Deliver seamless and integrated experiences across web and mobile that address the needs of their users.
You will have a strong customer focus to obsess over the users experience, and to ensure that every application and feature is designed with their needs and challenges in mind. You should prioritize empathy and understanding in every aspect of web and mobile development.
Collaborate effectively with cross-functional teams, which includes product management, design, marketing, and customer service.
Manage the engineering budget while optimizing resources to achieve maximum impact to ensure that the technology investments align with their mission.
Build, mentor, and lead a high-performing engineering team that includes a culture of collaboration, innovation, and continuous improvement.
You will guide the team in leveraging technologies to build scalable, robust, and user-friendly web and mobile applications.
Ensure that the platforms are reliable and accessible for all users by being a champion for quality assurance and software testing methodologies across web and mobile platforms to deliver exceptional user experiences and maintain the highest standards of code quality.
Knowledge of emerging technologies and industry trends relevant to their industry, web, and mobile development. Evaluate and implement new tools and techniques to enhance the customer-facing solutions and provide cutting-edge support for their users.
Qualifications:
Experience leading and mentoring engineering teams and e-commerce platform experience in both web and mobile development
Strong expertise in Next.Js, React, TypeScript, AWS Services, GCP, CI/CD pipelines (using GitHub Actions), release management tools (such as Vercel), and marketing technologies (like Google Tag Manager and Google Analytics).
Proven track record of delivering high-quality web and mobile software products within budget and timeline constraints, and a demonstrated commitment to efficiency and effectiveness.
Strong commitment to code quality, performance, and the overall user experience across web and mobile.
Exceptional analytical and problem-solving skills, with the ability to address complex challenges related to web and mobile development, and the ability to effectively communicate technical concepts to both technical and non-technical stakeholders.
Bachelor's or Master's degree in Computer Science or a related field.
All qualified applicants will receive consideration for employment without regard to race, color, national origin, age, ancestry, religion, sex, sexual orientation, gender identity, gender expression, marital status, disability, medical condition, genetic information, pregnancy, or military or veteran status. You must be legally authorized to work in the United States without current or future sponsorship.
My notes:
Role:
This role reports directly to the CTO and is a top priority role for them. You will lead the development and enhancement of their customer-facing applications (web and mobile), e-commerce store, and customer service back-office systems.
Outcomes:
and impacts we want them to have on business:
Launch e-commerce MVP ASAP:
Deliver the e-commerce MVP high-converting website experience that is customer first, simple, focused to customers and google bot as quickly as possible.
GTM and Marketing tags uptime:
Ensure all marketing and data platforms have consistent and high-quality data from our website in order to power customer acquisitions, retargeting efforts and personalization.
Up-time, scalability, site reliability and repeatability:
Ensure customers and CX always have access to a fast-performing site and tools.
Drive down friction to servicing customers:
Delivering time/cost saving features and tools to customers and our CX team to allow both parties to self-serve more efficiently.
Drive a high-performance (speed, quality, and reliability) culture aligned with Carewell’s values of customer-first, speed to market, simplicity, focus, accountability, professionalism and trust.
Must:
Deep understanding and hands on experience with Next.Js, React, TypeScript, AWS, GCP, CI/CD pipelines, and relevant marketing technologies. They must have a leadership ability, and can manage while being hands on. They need an architectural vision, and the ability to technical problem solve. They must have risk management, agile methodology proficiency and process optimization.
How much hands on coding will they be doing?
Is it 50/50 web vs mobile?
Is it just the customer facing applications, or will they helping in other areas as well?
Is this leading a full-stack team or is there a strong preference on the backend?
Is there a specific part of e-commerce that they need experience with the most?
Fall Short:

Why open:

Interview Process:
What does their team look like now and what will it look like in the future?
Additional Personalities other than what you see below under company notes:
Someone who is highly productive with a focus on urgent and quality delivery. They must have strong communication and documentation abilities. They should have good collaboration skills with a proactive and self-directed work style. They should be a hard worker that has the ability to work under pressure.
Salary:
$190K-$210K/year plus 5% bonus (equity of 20-30K options depending on salary)
Interview Process:
Submit resumes to Greenhouse, and the CTO will review. The COO or HR Manager will do culture screening (45min video interview), and then a tech interview with Sam (CTO) &
Ryan Martin (60min technical video interview). If that goes well, they will do a case study, which is an architecture challenge, followed by a scheduled meeting with Sam (CTO), Ryan, Bianca (CEO) and a Product Manager (1 hour panel video case study interview and a technical conversation). They want to know their experiences and what they would build. They can use AI tools if needed but be honest and just say that you used AI (someone in the past lied about it and it didn’t go well).
Company:
Website Description:
Their website is. Carewell is a category-defining business that is dedicated to providing the most trusted and reputable retail source for caregiving products. Our vast selection of expert-vetted products includes incontinence supplies, wound care, nutrition, mobility aids, and more, all available at the best prices with fast, reliable shipping. We are proud to have been recognized as one of the fastest-growing companies in the US, ranked on the Inc. 5000, and named one of the most customer-centric companies in the world by Forbes in 2022. At Carewell, we understand the importance of caregiving, and we strive to provide the highest quality products to help caregivers provide the best care possible for their loved ones. As the number of older adults in the US grows, the need for caregiving solutions will only increase. By joining Carewell, you will have the opportunity to work in a space that is constantly evolving, with new challenges and opportunities for growth. We are committed to being architects of our own success, always striving to improve our teams, partnerships, and solutions to ensure impact, scalability, and simplicity. As a member of our team, you will have the opportunity to collaborate with like-minded individuals, using customer insights, data, research, and feedback to make decisions and create the most effective solutions. If you are ready to join a team of dedicated individuals who are committed to making a difference in the world, Carewell is the place for you.
The Carewell story:
Our story began in 2015, when our co-founder and CEO Bianca helped her mom care for her grandmother. They had no clue which products they needed, much less where to find them or how to use them. Online marketplaces were confusing, local shops had limited selection and no discretion, and both experiences lacked empathy. Bianca was shocked there was no What to Expect guide like there is for new parents, so she and her husband/co-founder Jonathan dedicated their lives to creating a solution for family caregivers just like you. Here’s a great article about them at.
Overview:
They are an e-commerce first marketplace. It’s the chewy blueprint but instead of products for animals, it’s products for the elderly. They want to get into prescriptions and private label products like Chewy in the future too. In May 2024, they were at about $50-$100 million in revenue and they are looking to 10X that, which they believe is on the low end. They also closed a $25 million in series B in early 2024 that is for hiring. The former CFO at Chewy is on their board, and he’s the one that negotiated the $3.5 billion sale of Chewy. Plus, most of their leadership team is from Chewy, so they are looking to replicate that.
Upcoming Projects:
They are currently doing a revamp their e-commerce website, and they will look to add prescriptions and private labels in the future. They will likely add a mobile app down the line but fixing the website is the #1 priority. Their CEO is technical and originally put it together, but it is a lot of systems connected together.
Company size:
They have hired a ton of former Chewy leaders and have over 200 employees as of May 2024. They are looking to grow and expand that number. Some of the former Chewy leaders are their CFO, CTO, CMO (was VP of Growth), the VP of Marketing, Head of customer service, Head of merchandising, and others that lead analytics, direct mail and paid search, and the creative direction. They have double the amount of women in leadership than men.
Size of IT Team:
Currently there are 8-10 people. They have 4-5 on the front end, which is their storefront team. Ryan Martin is leading their backend team, and they have some people from Brazil helping for now. Daryl Altenhof is the Director of IT. They might build an infosec team, but Darryl is doing it now. They will be adding 3 Staff Engineers and an SRE. There is also someone in the UK, but I’m not sure what they do. The product and design team is currently under the CTO, but it’s moving to marketing under the VP of Brand, Andrea Wolfe. One person in the UIK.
Tech stack:
They use the GCP cloud, PostgreSQL, serverless GCP, typescript, and react on the front end. Same tech as BEX (loves Dierdre).
Remote/Onsite:
remote but EST is the preference. They can technically live anywhere but CA and NY aren’t a preference. They have daily 9am EST standups.
Benefits:
Competitive compensation, Health, Dental, and Vision insurance, Short-term Disability and Life Insurance (100% employer-sponsored), Supplemental Life Insurance (employee-sponsored), 401(k) Retirement Plan (no employer contribution), 100% Remote, company laptop and Employee discount. They have flexible PTO, with a soft cap at 20 days plus 6 paid holidays. Onsite opportunity in Miami up to 2x per year. Maternity leave is 13 weeks @ 100% and Parental leave (non-birthing parents) at 4 weeks @ 100%. They have 3 United Healthcare plans. The Base Plan (comes with HSA):
employee only covered at 80%, employee + spouse covered at 39%, employee + child/children covered at 49% and employee + family covered at 44%.
The Buy Up Plan:
employee only covered at 70%, employee + spouse covered at 34%, employee + child/children covered at 48% and employee + family covered at 37%.
Buy Up Plan 2:
employee only covered at 64%, employee + spouse covered at 31%, employee + child/children covered at 57%, and employee + family covered at 48%.
Guardian Dental:
Covered at 75% of employee only
Guardian Vision:
Covered at 75% of employee only
Guardian STD provided at no cost to employee, Guardian LTD, Guardian basic life &
AD&
D at no cost to employee and Guardian supplemental basic life &
AD&
D.
Hiring/Staffing:
Their career page is. They used Tech Recruiters before, but they were not producing. Plus, people tried to negotiate too much at the end. They asked the CTO who to use and she immediately asked for us. They don’t want to renegotiate with candidates at the end. They like a pipeline of candidates, in case someone falls off. They don’t want to have to start the search again. They targeted Wayfair (too expensive) and chewy. Working for Shopify is a big plus.
Offers:
There is no bonus for roles under director. They will get 2 offers to choose from with different stock options and they will not renegotiate. For the higher base salaries, they will get 15K in stock options. The stock value for 15K in stock options is about $52K in today’s value, but if they get to a 10x and $500 million acquisition, that would be $520K. For a mid-level salary offers, they’d get 20K in stock. The stock value for 20K in stock options is about $87.5K in today’s value, but at 10X growth and acquisition, that puts it at $875K. At a lower salary, they’d get 25K in stock. Chewy sold at $3.5 billion with the same team, and they have no doubt this will be in that ballpark too.
Personalities:
They want people that get things done, have a low ego, can take responsibility, and have an ownership mindset. They have a strong “cameras on” culture, and they are highly communicative with a lot of humor. They like people that have experience in a startup and working with a lean team. Also, someone that is ok with on-call support outside of typical working hours. There is a lot of work, and they want a hard worker that can be productive quickly. Someone who can see what the problems are and can solve them. They like self-starters that don’t need a lot of hand holding. E-commerce experience is important, and they ideally want someone who’s recently worked for an e-comm first platform.
Carewell Competencies:
Customer first, simple, high impact only, scalable, frugal and high bar.
Headquarters:
South Florida
Competitors:
Hiring Managers:
O Sam Rassner (CTO):
Her LI is. Her meeting scheduler is at this link:
. Just as a heads up, she’s usually 5-10 minutes late, so please let us know if she’s running late, so we can ping her. I’ve known her since she was at Chewy. We placed her at BEX and then filled multiple positions for her at BEX and Emed. She is a leader, a builder, a thinker, and an engineer with experience from idea to product launch. She loves leading technology teams at SaaS companies and started as a Software Engineer herself. She is not only a phenomenal CTO, but she can get her hands dirty with technology and could step in to be an Architect if needed. Sam loves building products and working for a company that appreciates technology. She has strong experience building and running teams in the software space, and her specialty is helping early startup software companies build. She understands business value and can bring together excellent teams that can work miracles and enjoy each other. She also has strong cloud experience with AWS and Google. Sam’s technical and leadership skills are incredible, but what really sets her apart is her personality. She is someone who never loses sight of the company’s mission and goals. She can build a world class organization, and then lead that organization to record breaking success. Sam is detail driven and technically knowledgeable. She will push her team to be the best versions of themselves that they can be, and she will never ask them to do more than she herself is already doing with her incredible work ethic. She’s a workaholic that any team can rally behind and a huge value to any company she’s worked for. Sam’s work background:
Sam was the VP of Software Development at Chewy, an e-commerce pet store with more than 100,000 pet products and Rx pet medications. She was vital in helping them grow from a startup to where they are today and grew the development team from 6 developers to 120 in 2.5 years. She led multiple departments, multiple locations, and high scale development that covered end-to-end ecommerce systems. She collaborated across IT departments and created a DevOps organizational structure across all teams. She even led the Agile Transformation and brought them from a start-up style software team to a mature software team using Agile Methodologies using Scrum, KanBan, and ScrumBan. After Chewy, she missed the smaller team she had at Chewy and wanted to help another startup grow. She then joined BEX Realty as their CTO, and led a technical team similar in size to what she started with at Chewy. BEX Realty is a nationwide, technology-driven real estate firm. She loved it there, and loved her team, but was recruited to take over as the CTO at eMed. This was a fantastic opportunity to not only lead this innovative SaaS startup in the healthcare space, but to help save lives during the Covid pandemic. She has remained close with BEX and is their Technical Advisor when needed. She then became the CTO at eMed which is democratizing healthcare with a digital point-of-care platform for at-home healthcare testing. They were focused on the global COVID-19 pandemic, and have provided tens of millions of virtually-proctored at-home COVID-19 tests. They were trying to restructure post covid, and they had plans to expand its technology to other use cases and common illnesses in the future. Their software and testing products could include drug screening, lime disease, sinus, covid/flu, strep throat, etc. She ended up leaving there, because they were restructuring and considering putting technology in maintenance mode. They have such potential and great products, but they don’t understand what they have and the talented people on their team.
Tarah Kendall (HR Manager):
Her Linked In is. She was a Branch Manager at Enterprise before coming to Carewell in 2021. She lives in VA and she is very nice.
Jonathan Magolnick (COO &
Co-Founder):
His Linked In is. Jonathan is an efficient, analytic, tech-savvy business professional, who obtained his MBA in May 2017. He has significant experience in contract negotiation, sales, and account management, and has owned and operated a medical supply company since August 2015. He has business acumen with outstanding relationship building skills, business development experience, and exceptional writing and communication abilities that maximize organizational needs. Jonathan is recognized for critical thinking, collaborative work processes, and excelling in fast-paced environments while meeting time sensitive deadlines. He is bilingual in English and Spanish. He went to the University of Miami and got his MBA there. Then he was a sports staff writer and then worked at FOX Sports in add sales and programming &
acquisitions. He’s beenat Carewell since Aug 2015 and Co-founded the company with his wife, Bianca.
Bianca Padilla (CEO &
Co-founder):
Her Linked In is. She started this company with her husband, Jonathan Magolnick. She went to NYU and worked in Private Equity and was a software engineer prior. CEO and co-founder of Carewell, a family-founded company that simplifies life for caregivers by providing personalized service, compassionate content, and expert-vetted home care products. Graduate of NYU and the Disney Institute. Founder and ambassador of the Charlotte chapter of Aging 2.0. Miami native, traveler, foodie, and reader of books about entrepreneurship, leadership, tech, and comedy - open to recommendations!
Ryan Martin:
His Linked In is. He’s a strong data guy and is leading the backend engineers under the CTO. He came over from eMed.
Daryl Altenhof:
His Linked IN is. He’s the Director of IT and came over from eMed. We placed him at eMed. He’s leading IT and doing infosec for now.
Andrea Wolfe (VP of Brand):
Her LI is. She lives in Austin, TX. She was formerly the VP of Marketing at Chewy, and has held marketing and brand leadership roles at Spreetail, Outdoorsy, and GameStop. She is an Ecommerce marketing executive leading brand marketing, performance marketing, growth marketing, and customer experience teams. She develops online content to educate and engage audiences that leads to conversion and builds captivating social communities and brand advocate platforms. She has experience achieving maximum impact in changing, growing, decentralized cultures. She is a strategic thinker who can collaborate with a diverse set of stakeholders. Strengths Finder:
Command - Futuristic - Intellection - Positivity - Includer. She loves dogs, yoga, eating plant-based foods (and BBQ), reading, and travel. Specialties:
advertising agency, broadcast, budgeting, creative direction, customer relations, marketing, merchandising, sales, strategic marketing, QSR, new business development, consumer promotions, direct marketing, ecommerce, retail
Original Job Description:
Are you a data-driven problem solver who is passionate about making a difference in the lives of others while contributing to a fast growing start-up? Join Carewell and be a part of a team that creates impactful solutions for caregivers and their unique challenges. We're looking for hardworking individuals committed to raising the bar and striving for impact, scalability, and simplicity. Build your career with Carewell, a category-defining business dedicated to making caregiving easier.
The importance of hiring a Director of Engineering, E-Commerce Apps
Carewell is seeking a visionary Director of Engineering to lead the development and enhancement of our customer-facing applications (web and mobile), e-commerce store, and customer service back office systems. If you are a passionate technologist with a proven track record of building high-performing teams and driving impactful results, we want to hear from you. This role will report directly to the CTO.
What you’ll do:
Technical Leadership:
Provide technical leadership and strategic direction for the development of all customer-facing applications, including web and mobile platforms, e-commerce store, and customer service tools. Ensure alignment with overall business goals and objectives to enhance the caregiving experience.
Team Management:
Build, mentor, and lead a high-performing engineering team. Foster a culture of collaboration, innovation, and continuous improvement, reflecting Carewell's values of compassion and support.
Technology Expertise:
Demonstrate expertise in Next.Js, React, TypeScript, AWS Services, Google Cloud Platform (GCP), CI/CD pipelines (ideally using GitHub Actions), release management tools (such as Vercel), and marketing technologies (like Google Tag Manager and Google Analytics). Guide the team in leveraging these technologies to build scalable, robust, and user-friendly web and mobile applications that meet the unique needs of caregivers.
Quality Assurance:
Champion quality assurance and software testing methodologies across web and mobile platforms to deliver exceptional user experiences and maintain the highest standards of code quality, ensuring that our platforms are reliable and accessible for all users.
Customer Focus:
Obsess over the caregiver and care recipient experience, ensuring that every application and feature is designed with their needs and challenges in mind. Prioritize empathy and understanding in every aspect of web and mobile development.
Performance Optimization:
Drive performance optimization initiatives across web and mobile platforms to ensure fast and responsive applications, resulting in increased caregiver satisfaction and engagement with our platforms.
Innovation:
Stay abreast of emerging technologies and industry trends relevant to the caregiving space, web, and mobile development. Evaluate and implement new tools and techniques to enhance our customer-facing solutions and provide cutting-edge support for caregivers.
Collaboration:
Collaborate effectively with cross-functional teams, including product management, design, marketing, and customer service, to deliver seamless and integrated experiences across web and mobile that address the holistic needs of caregivers.
Budget Management:
Manage the engineering budget, optimizing resources to achieve maximum impact and ensuring that our technology investments align with Carewell's mission.
What you’ll need:
Engineering Background:
Bachelor's or Master's degree in Computer Science or a related field.
Proven Leadership:
Demonstrated experience leading and mentoring engineering teams, fostering a positive and collaborative work environment that reflects Carewell's values.
Technical Expertise:
Deep expertise in Next.Js, React, TypeScript, AWS Services, GCP, CI/CD pipelines (ideally using GitHub Actions), release management tools (such as Vercel), marketing technologies (like Google Tag Manager and Google Analytics), and e-commerce platforms, with experience in web and mobile development.
Quality Obsession:
Unwavering commitment to code quality, performance, and the overall user experience across web and mobile, aligning with Carewell's dedication to excellence.
Results-Oriented:
Proven track record of delivering high-quality web and mobile software products within budget and timeline constraints, demonstrating a commitment to efficiency and effectiveness.
Problem-Solving:
Exceptional analytical and problem-solving skills, with the ability to address complex challenges related to the caregiving industry, web, and mobile development.
Communication:
Excellent written and verbal communication skills, capable of effectively communicating technical concepts to both technical and non-technical stakeholders, fostering understanding and collaboration.