Product Success Engineer

Who We Are 

Cobalt was founded on the belief of a fundamental human aspiration: the desire to live better and safer. It all started in 2013, when our founders realized that pentesting can be better. Today our diverse, fully remote team is committed to helping organizations of all sizes with seamless, effective and collaborative Offensive Security Testing that empower organizations to OPERATE FEARLESSLY and INNOVATE SECURELY.

Our customers can start a pentest in as little as 24 hours and integrate with advanced development cycles thanks to the powerful combination of our SaaS platform coupled with an exclusive community of testers known as the Cobalt Core. Accepting just 5% of applicants, the Cobalt Core boasts over 400 closely vetted and highly skilled testers who jointly conduct thousands of tests each year and are at the forefront of identifying and helping remediate risk across a dynamically changing attack surface.

Cobalt is an Equal Opportunity Employer and we strive to build a diverse and inclusive workforce at our company. At Cobalt we aspire to engage with diverse individuals, communities, and organizations in order to continue to nurture our unique rich diverse culture. Join our team, and be your true self to do your best work. 

Description

As a Product Success Engineer at Cobalt, you will shape and scale our support processes, documentation, tools and workflows. Part of your time will be dedicated to directly supporting our customers and staff by triaging inquiries from various channels, providing Level 1 support (via chat, email, or video calls) for common inquiries or facilitating and tracking escalation flows. The rest you’ll focus on enhancing our support efficiency and effectiveness by continually improving self-service channels, such as our customer-facing and internal product documentation, tuning AI/LLM systems to provide quality and reliable guidance, and collaborating with business and product teams on platform or operational improvements to address common support issues. 

Our ideal candidate is passionate about customer support, excels in problem-solving, and brings a proactive mindset, always seeking ways to optimize or automate processes to get customers the answers they need faster while enabling our teams to focus on new and bigger challenges. 

This role will work remotely, but must be located in the US Eastern timezone, available from 8am to 5pm ET. 

What You'll Do

• Support Excellence: Triage customer and internal support inquiries, directly providing Level 1 support or escalating to appropriate teams, and tracking cases to ensure quick and effective resolution. Common issues you’ll support with may include:

1. Consulting customers on how to best utilize, customize and implement Cobalt’s integration and API solutions
2. Helping users optimize their configuration of our automated security tools to maximize coverage and efficacy for their applications
3. Assisting customers with connecting their identify management systems, configuring access controls, or troubleshooting login issues 
4. Facilitating operational workflows and coordinating internal approvals 

• Support Process & Tooling: Design, operationalize, and maintain scalable support processes and tooling for case management, escalations, tracking and reporting.  
• Knowledge Management: Maintain our product documentation, ensuring our documentation follows best practices, and continually updating content with troubleshooting guides and self-service materials that enable customers and staff to get answers when they need them and limiting support touchpoints. 
• In-App Help Desk: Collaborate closely with Software Engineers to integrate a help desk solution, including an AI-driven chat support bot, into our platform and data reporting systems.  
• Change Management:  Partner with the Product team to prepare announcements, documentation, FAQs and release notes for new product launches, and continually update internal materials to enable sales and customer success teams to effectively support the product. 
• Cross-Functional Collaboration: Work with various teams to understand support needs, and share insights and solutions to common customer/internal challenges to inform product improvements and innovation.
• Inform Product Improvements:  Consolidate insights and feedback on customer pain points to help inform product improvements and roadmap. 

You Have

• Proven Expertise: Minimum of 3 years of technical product support experience. 
• Technical Writing: Expertise with technical writing, able to communicate complex and technical concepts in simple ways, in the form of product documentation, in-app content, how-to guides, diagrams, playbooks and other supporting materials. 
• Ticketing Tools:  Proficiency with configuring, integrating and operating support and development ticketing systems such as Jira, Github, and Zendesk.
• Problem Solving: Excellent problem-solving skills, with the ability to interpret data and derive actionable insights.
• Stakeholder Management:Excellent verbal and written communication skills, enabling effective collaboration in a remote setting, and the ability to build relationships across functions.
• Entrepreneurial Mindset: Eagerness to learn new technologies and approaches, with a proactive mindset and willingness to contribute ideas.

Nice to have

• DevSecOps Proficiency:  Fluency with development, security and reporting tools, such as Google BigQuery, Looker Studio, ServiceNow, Github, PowerBI, etc. 
• Workflow Automation: Experience with low-code/no-code automation tools, such as Workato and Zapier.
• Programming: Familiarity with coding frameworks, such as Python, Javascript, SQL. Understanding of how REST APIs work, and how to interact with an API using a tool like Postman. 
• AI and ML Knowledge:  Understanding of Machine Learning and Generative AI. 

Why You Should Join Us

• Grow in a passionate, rapidly expanding industry operating at the forefront of the Pentesting industry 
• Work directly with experienced senior leaders with ongoing mentorship opportunities
• Earn competitive compensation and an attractive equity plan
• Save for the future with a 401(k) program (US) or pension (EU) 
• Benefit from medical, dental, vision and life insurance (US) or statutory healthcare (EU)
• Leverage stipends for:
• Wellness
• Work-from-home equipment & wifi
• Learning & development
• Make the most of our flexible, generous paid time off and paid parental leave 

Pay Range Disclosure(For US openings only)

Cobalt is committed to fair and equitable compensation practices. The salary range for this role is ($96,800- $121,000) per year + equity + benefits. A candidate’s salary is determined by various factors including, but not limited to, relevant work experience, skills, and certifications.  The salary range may differ in other states and may be impacted by proximity to major metropolitan cities. 

Cobalt (the "Company") is an equal opportunity employer, and we want the best available persons for every job. The Company makes employment decisions only based on merit. It is the Company's policy to prohibit discrimination in any employment opportunity (including but not limited to recruitment, employment, promotion, salary increases, benefits, termination and all other terms and conditions of employment) based on race, color, sex, sexual orientation, gender, gender identity, gender expression, genetic information, pregnancy, religious creed, national origin, ancestry, age, physical/mental disability, medical condition, marital/domestic partner status, military and veteran status, height, weight or any other such characteristic protected by federal, state or local law. The Company is committed to complying with all applicable laws and providing equal employment opportunities. This commitment applies to all persons involved in the operations of the Company regardless of where the employee is located and prohibits unlawful discrimination by any employee of the Company.

Cobalt is an E-Verify employer. E-Verify is an Internet-based system operated by the Department of Homeland Security (DHS) in partnership with the Social Security Administration (SSA). It allows participating employers to electronically verify the employment eligibility of their newly hired employees in the United States.

About the Team

At Stitch Fix, we believe in transforming the way people find what they love by combining technology, data science, and the human instincts of a Stylist. The Learning & Playback (L&P) team plays a crucial role in this mission, focusing on driving deeper personalization and understanding of our clients. Our goal is to elicit client style preferences and taste and to “learn” who they are, what they like and don’t like, and “playback” what we’ve understood, enabling clients to correct us, and help us to refine their personalized shopping experience. This approach allows us to deliver industry-leading styling and shopping experiences, grounded in the most advanced machine learning and AI capabilities.

About the Role

We are seeking a strategic and experienced Data Science Product Manager to lead our Learning & Playback team. In this highly strategic and impactful role, you will define the product strategy and vision that bridges data science, client needs, and business objectives. You will partner closely with Data Science, Engineering, Design, and other Product Managers to deliver on a roadmap that enhances our understanding of client preferences and improves the personalization of our recommendations.

You're excited about this opportunity because you will…

• Develop and execute a product strategy that enhances our best-in-class understanding of client fashion taste and styling preferences, personalization, and the ability to deliver exceptional styling experiences. This includes leveraging cutting-edge Gen AI capabilities to drive improvements in our recommendation systems.
• Own the roadmap, informed by data-driven insights and advanced analytics, to prioritize investments in machine learning capabilities and product features that serve our clients' needs and drive business value.
• Identify and articulate clear, strategic problem statements, translating complex business challenges into focused opportunities that push the boundaries of personalization and client satisfaction.
• Collaborate with Data Scientists, Engineering, and Design to leverage cutting-edge AI capabilities, driving enhancements in our recommendation systems to create experiences where clients discover styles they love, fit perfectly, and help them always look—and feel—their best.
• Lead with influence, not just authority, fostering a collaborative environment where diverse perspectives from Data Science, Engineering, and Design come together to solve complex challenges and build exceptional products.
• Shape the future of AI-driven personalization at Stitch Fix, with the opportunity to take on high-visibility projects and grow into a key leadership role within the product organization.
• Drive key initiatives and projects, such as StyleFile Expansion, Conversational Onboarding, Style Shuffle V2, and improvements in core recommendation models.
• Continuously learn and gather feedback from clients, iterating on our style quiz, profile updates, and integrating these learnings into both the Fix and Freestyle experiences.
• Improve item recommendations and surfacing, ensuring clients receive personalized, high-quality recommendations that align with their preferences and style needs.

We’re excited about you because…

• You have 5-8 years of product management experience, with a strong focus on data science, machine learning, and recommendation systems.
• You are a strategic thinker who can synthesize customer needs, industry trends, and company objectives to create a compelling vision and a long-term strategy for Learning & Playback.
• Champion client empathy and build robust feedback loops, integrating client insights into every stage of product development to ensure our AI-driven experiences feel personal, relevant, and delightful.
• You embody our Stitch Fix values—bright, kind, and motivated by challenge—and who approaches every problem with curiosity, accountability, and a desire to learn.
• You have repeated success in driving conversion, engagement, or retention by leading major product initiatives, driving cross-functional teams, and delivering meaningful customer value.
• You possess a deep understanding of data analytics and the ability to collaborate effectively with Data Science and Engineering teams, translating business goals into actionable ML projects.
• You are skilled in prioritization and stakeholder management, comfortable navigating differing opinions, setting expectations, and ensuring alignment across teams.
• Bonus points for experience in eCommerce recommendation systems, early-stage product development and obsessing over the cutting edge of Generative AI.

Why you'll love working at Stitch Fix...

• We are a group of bright, kind people who are motivated by challenge. We value integrity, innovation and trust. You’ll bring these characteristics to life in everything you do at Stitch Fix.
• We cultivate a community of diverse perspectives— all voices are heard and valued.
• We are an innovative company and leverage our strengths in fashion and tech to disrupt the future of retail. 
• We win as a team, commit to our work, and celebrate grit together because we value strong relationships.
• We boldly create the future while keeping equity and sustainability at the center of all that we do. 
• We are the owners of our work and are energized by solving problems through a growth mindset lens. We think broadly and creatively through every situation to create meaningful impact.
• We offer comprehensive compensation packages and inclusive health and wellness benefits.

As Sr. Data Scientist II, you’ll empower the design, development, and optimization of AI/ML models based on industry best practices. Drive progress of AI/ML components used in DoD Search Portfolio products.

We know that you can’t have great technology services without amazing people. At MetroStar, we are obsessedwithour people and have led a two-decade legacy of building the best and brightest teams. Because we know our future relies on our deep understanding and relentless focus on our people, we live by our mission: A passion for our people. Value for our customers.

If you think you can see yourself delivering our mission and pursuing our goals with us, then check out the job description below!

What you’ll do:

• Designs, configures, develops, tests, and supports informatics and data science solutions for a wide array of technical use cases;
• Collaborate with cross-functional teams, including data scientists and software engineers to integrate AI solutions developed by other elements of CDAO or the DoD community into Search Portfolio products when appropriate
• Optimize AI models for performance, scalability, and efficiency, leveraging cloud-based resources and distributed computing frameworks, specifically Apache Spark/Databricks. Ability to adapt code base to also run using GPU enabled Kubernetes clusters.
• Stay updated on and contribute to the latest advancements in AI research, applying new findings to improve Search Portfolio products
• Manage the lifecycle of AI/ML components used in Search Portfolio products from research and development to deployment and optimization
• Applies analytical methodologies to diagnose data-related challenges, implement solutions, and evaluate performance;
• Documents and presents requirements, design alternatives, and findings to team members and clients;
• Ability to develop strategic, baselined, data modeling processes; ability to accurately determine cause-and-effect relationships; and
• Experience with integrated development environments, data integration, data visualization, data mining, and analysis tools.
• Maintains and guides the development of common libraries and tools used by multiple teams.
• Aids in formulating a strategy on how to achieve rapid prototyping

What you’ll need to succeed:

• Bachelor’s degree plus 7-10 years of data science experience, or a Masters Degree plus 5 years of data science experience.
• Active Top Secret clearance with the ability to obtain a SCI
• Experience with ML fields, e.g., natural language processing, computer vision, statistical learning theory
• Hands-on experience with Natural Language Processing (NLP), Large Language Models, text embedding, semantic query, use of generative AI for text, and retrieval augmented generation (RAG)
• Familiarity with data preprocessing, feature engineering, and model evaluation techniques essential for machine learning projects
• Strong understanding of various machine learning algorithms, including supervised and unsupervised learning, reinforcement learning, and neural networks
• Experience with version control systems like Git, enabling effective collaboration and code management
• Experience in an ML engineer or data scientist role building ML models
• Experience writing code in Python, R, Scala, Java, C++ with documentation for reproducibility
• Experience using Apache Spark/Databricks distributed compute environments for AI/ML workloads
• Experience handling petabyte size datasets, diving into data to discover hidden patterns, using data visualization tools, writing SQL, and working with GPUs to develop models
• Experience with cloud-based data persistence products, especially RDS PostgreSQL and PostgreSQL extensions such as pgvector.
• Experience writing and speaking about technical concepts to business, technical, and lay audiences and giving data-driven presentations

Like we said, we arebig fans of our people. That’s why we offer a generous benefits package, professional growth, and valuable time to recharge. Learn more about our company culture codeand benefits. Plus, check out our accolades.

Don’t meet every single requirement? 

Studies have shown that women, people of color and the LGBTQ+ community are less likely to apply to jobs unless they meet every single qualification.  At MetroStar we are dedicated to building a diverse, inclusive, and authentic culture, so, if you’re excited about this role, but your previous experience doesn’t align perfectly with every qualification in the job description, we encourage you to go ahead and apply.  We pride ourselves on making great matches, and you may be the perfect match for this role or another one we have. Best of luck! – The MetroStar People & Culture Team

What we want you to know:

In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification form upon hire.

MetroStar Systems is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. The statements herein are intended to describe the general nature and level of work being performed by employees and are not to be construed as an exhaustive list of responsibilities, duties, and skills required of personnel so classified. Furthermore, they do not establish a contract for employment and are subject to change at the discretion of MetroStar Systems.

Not ready to apply now?

Sign up to join our newsletter here.

About the Role:

Gusto’s Data Science team leverages Gusto’s rich dataset to guide product direction and decision-making. We operate full-stack, conducting analyses, prototyping and deploying predictive models and statistical tools both for internal use and for our customers. 

For this role, we are looking for a technical leader (an individual contributor) to drive machine learning and AI in the payment and risk domains.  You will build a model-driven risk platform to provide a trusted environment for Gusto Ecosystem. 

You’ll be working with an established team and seasoned payments and risk leaders in Engineering, Product, Design, Operation, Identity and Compliance. In this role, you’ll work cross functionally to build Platforms that span the entire breadth of the Payments and Risk Stacks, and use ML and AI to build a world- class, high secure platform that safeguards our users’ activities and money, and ensures unparalleled reliability. 

Here’s what you’ll do day-to-day:

• Build and deploy machine learning models to identify, assess and mitigate risks 
• Responsible for driving research in the problem space, working with stakeholders to understand model requirements, developing the model from scratch, deploying the model alongside your engineering counterparts, and monitoring and maintaining the model’s performance over time
• Partner with Engineering, Design, and Product counterparts in Payment and Risk to solve complex cross functional problems
• Develop scalable frameworks and libraries that enhance and contribute to the team’s core analysis and modeling capabilities
• Identify new opportunities to leverage data to improve Gusto’s products and help risk management team to understand business requirements  and develop tailored solutions 
• Present and communicate results to stakeholders across the company

Here’s what we're looking for:

• 8+ years experience conducting statistical analyses on large datasets and deep domain knowledge in machine learning. 
  • This could mean either a MS or PhD in a quantitative field with at least 5 years experience in a business environment, or BS or Data Science Bootcamp graduate with at least 8 years of experience working as a data scientist or a machine learning engineer in a business setting.
• Experience applying a variety of statistical and modeling techniques using Python, R or another statistical modeling language, as indicated by familiarity with many of the following techniques - predictive modeling, anomaly detection, ensemble methods, natural language processing (NLP, optional).
• Strong programming skills - comfortable with all phases of the data science development process, from initial analysis and model development all the way through to deployment
• Excellent communication skills - able to effectively deliver findings and recommendations to non-technical stakeholders in a clear and compelling fashion
• PhD or Masters plus equivalent experience in a quantitative field is a plus
• Experience in the Fintech industry or risk management domain is a plus

Our cash compensation amount for this role is targeted at $195,000-$241,000/year in New York and $177,00- $219,000/year CAD in Toronto. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

Overview

About the Role:

This is a general posting for multiple Sr. Machine Learning roles open across our 4-sided marketplace. You’ll get the chance to learn about the problems the different ML teams solve as you go through the process. Towards the end of your process, we’ll do a team-matching exercise to determine which of the open roles/teams you’ll join. You can find a blurb on each team at the bottom of this page. 

With regards to level, we have flexibility. Your level will be determined by your education, years of experience, and most importantly, how you perform throughout the interview process.

About the Team:

You will be joining our team and will tackle some of the most challenging and impactful problems that are transforming how people buy groceries every day.  We’re looking for a self-driven, strategic thinker who can hit the ground running to ultimately influence decision-making across the entire organization.

About the Job:

• Design, develop, and deploy machine learning solutions to tackle practical challenges in the our complex marketplace.
• Collaborate closely with product managers, data scientists, and backend engineers to deeply understand business needs and create impactful ML applications.
• Actively engage with diverse stakeholders to ensure that solutions are well-integrated and aligned with business goals.
• Push the envelope on our operational efficiency by continually refining and advancing our algorithms and models.

About You:

Minimum Qualifications:

• Have a graduate degree (masters or PhD) in artificial intelligence, machine learning, operations research or equivalent self study and experience
• Have strong programming skills in Python and fluency in data manipulation (SQL, Pandas) and Machine Learning (scikit-learn, XGBoost, Keras/Tensorflow) tools
• Have strong analytical skills and problem-solving ability
• Are a strong communicator who can collaborate with diverse stakeholders across all levels

Preferred Qualifications:

• Have 5+ years of industry experience using machine learning to solve real-world problems with large datasets
• Knowledge of deep learning frameworks and methodologies
• Experience in productionalizing  machine learning and optimization techniques to solve marketplace problemm

OPEN ROLES:

Ads Marketplace: 

The Ads Marketplace team is responsible for the systems and algorithms for showing the right ad to the right user at the right time to balance user value, advertiser value, and instacart revenue. The team optimizes a multi-sided marketplace to ensure customers see ads that help them try new products/brands, advertisers get their products in front of appropriate users for a good return on investment, and instacart generates the deserving revenue as well. The team tackles hard problems in a variety of spaces, such as ranking, pricing, personalization, UX as well as foundational problems executing on a high throughput system with dynamic data. You'll develop and enhance Instacart's ads systems together with senior members of product & software engineering. You will use machine learning to devise and refine solutions throughout the ads auction such as ads selection, ranking, and pricing for all of Instacart’s consumer facing pages such as: search, storefront, aisle, pre and post checkout experiences, among many others. 

Overview

About the Role

This role offers the opportunity to put technical expertise and leadership skills towards driving high impact in programs that enhance our products, platforms, and the experiences of millions of customers, shoppers, retailers, advertisers, and the broader developer community. As a (Senior) Staff Technical Program Manager at Instacart, you will be at the forefront of our mission to transform the industries across grocery, retail, and restaurants by delivering on Instacart’s most complex and impactful efforts. You will be the owner of programs and associated business and technical outcomes, working closely with cross-functional teams across Engineering, Product, Data Science, Product Design, Business Development, Marketing, and others to define success, the strategy, requirements, track key metrics, lead execution, mitigate risks, and deliver on time with high quality outcomes. We are looking for driven individuals who thrive in a fast-paced Engineering environment, are passionate about quality and team performance, and feel comfortable making decisions on scope and technical trade-offs as well as building executive-level narratives. You will be required to operate independently, identify issues and opportunities proactively, lead from the front and by example, and be seen as a leader by senior leadership as well as various cross-functional teams across the broader organization.

Every day we solve increasingly complex business and technical problems that involve deep thinking and cross-functional collaboration to tackle. You will drive towards outcomes that have incredibly high impact across each of our 4-sided marketplaces: customers, shoppers, brands, and retailer partners. You will set the bar for what it means to deliver first-class, high quality experiences for our customers. Join us in this opportunity to lead a digital transformation of the industry by building technology that’ll power the next wave of innovative, scalable, and robust experiences to our customers.

About the Team

The Technical Program Management team is an integral part of the Instacart R&D organization. TPM operates within Engineering but drives priorities independently, so we align ourselves with the company’s highest priorities, biggest tech and product challenges, and our role strengths. Our team tackles some of the meatiest problems as we lead Instacart’s products, platforms, and operational excellence forward. Our work and its impact spans all sides of the marketplace: from using advanced ML to offer highly personalized replacements for out of stock items, to helping people save money through coupons and deals for their favorite brands, to unlocking innovative ways to shop for and deliver groceries, to evolving our ML tech stack and data infra, and so much more. We are seen as trusted thought partners to deliver on Instacart’s strategy at scale and enable strong cross-team and functional collaboration that results in teams across the company to achieve more together.

About the Job 

• You are seen as a leader within the Instacart consumer space, and seen as a trusted thought partner to organizational and cross-functional leaders.
• You “see around corners”, inform priorities, and are sought after to undertake the most challenging, unscoped problems.
• You lead the strategy, planning, roadmap, and technical execution of XL-sized programs with a high degree of uncertainty, ambiguity, complexity, and visibility.
• You are a natural key partner and influencer with Engineers, Product Managers, Product Designers, Data Scientists and other cross-functional partners to define outcomes, key results, and path to deliver. You define and deliver on requirements and execution plans, and manage an overall program's progress and outcome.
• You own clear and effective communication with stakeholders, including senior leadership, while raising priorities, risks, and course changes independently and proactively. You have shown you can influence decisions by senior leaders.
• You create a win-win by growing the pie. You foster a culture of teamwork and shared goals, create a collaborative and motivating team environment, and drive the right balance of process and velocity to ensure efficient, high quality, yet timely delivery.
• You are not only seen as a clear leader within TPM, but you regularly contribute more broadly to Instacart’s success by suggesting and driving organization-wide initiatives as well as mentoring and coaching others around you.

About You

Minimum Qualifications

• 10+ years of post-graduation experience in a technology field, preferably as a technical program manager, product manager, software engineer or engineering manager (technical domain), or related technical discipline.
• Experience in defining, delivering, derisking, and clearly exhibiting a combination of product and engineering prowess. You can clearly demonstrate how you are an angle-changer to outcomes.
• Can wear multiple hats to create strategy memos, write functional specs, define high level technical requirements, derive insights from structured data, and leverage LLMs as a productivity multiplier in addition to defining program structure & strategy.
• Experience in managing complex, ambiguous, multi-org programs end-to-end, from early conceptualization and definition to launch, throughout a software development lifecycle.
• A strong communicator, collaborator, and natural storyteller. You can distill multiple streams of information, convey priorities and risks, and build a strong narrative for stakeholders. 
• Bring executive presence with senior leaders. You are comfortable writing detailed plans as well as upleveling to an executive-level deck.
• Show strong ownership, accountability, and intellectual curiosity to understand executional and technical problems in depth, identify potential issues, and proactively incorporate mitigations into a realistic plan.
• Exhibits a growth mindset, can give and receive ongoing feedback, and can swiftly adapt to operating norms across diversity of teams.
• Bachelor's degree or greater in a technology or engineering discipline.

Preferred Qualifications

• Master’s degree in a technology or engineering discipline.
• Demonstrated ability to manage a cross-functional team of technical professionals.
• Shown ability to advocate and land architectural and technical decisions at the highest engineering leadership levels.

The salary range for this role is $50,000 - $120,000 per year (Gross in USD) 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a talented and motivated Principal Machine Learning Engineerwho is best in class with a high IQ plus a high EQ. This role presents an exciting opportunity to thrive in a dynamic, fast-paced environment within a rapidly growing team, with abundant prospects for career advancement.

You will be responsible for overseeing the design, development, and deployment of machine learning models that power and enhance our financial platform. In this role, you will drive the creation of scalable machine learning solutions for personalized recommendations in the Sezzle marketplace, fraud detection, and credit risk assessment, utilizing a combination of cloud services, open-source tools, and proprietary algorithms.

Your leadership will be key in blending machine learning development and operations (MLOps) to automate and optimize the full lifecycle of our ML models. You will collaborate with a team of engineers and data scientists to build large-scale, high-quality solutions that address diverse challenges in the shopping and fintech space. You’ll ensure our AI-driven features are robust, efficient, and scalable as we continue to grow.

Responsibilities:

• Design, Build, and Maintain Scalable ML Infrastructure: Lead the design and development of scalable machine learning infrastructure on AWS, utilizing services like AWS Sagemaker for efficient model training and deployment.
• Collaborate with Product Teams: Work closely with product teams to develop MVPs for AI-driven features, ensuring quick iterations and market testing to refine solutions effectively.
• Develop Monitoring & Alerting Frameworks: Create and enhance monitoring and alerting systems for machine learning models to ensure high performance, reliability, and minimal downtime.
• Support Cross-Departmental AI Utilization: Enable various departments within the organization to leverage AI/ML models, including cutting-edge Generative AI solutions, for different use cases.
• Provide Production Support: Offer expertise in debugging and resolving issues related to machine learning models in production, participating in on-call rotations for operational troubleshooting and incident resolution.
• Scale ML Architecture: Design and scale machine learning architecture to support rapid user growth, leveraging deep knowledge of AWS and ML best practices to ensure robustness and efficiency.
• Mentor and Elevate Team Skills: Conduct code reviews, mentor team members, and elevate overall team capabilities through knowledge sharing and collaboration.
• Stay Ahead of the Curve: Stay updated with the latest advancements in machine learning technologies and AWS services, driving the adoption of cutting-edge solutions to maintain a competitive edge.

Minimum Requirements:

• Bachelor's degree in Computer Science, Computer Engineering, Machine Learning, Statistics, Physics, or a relevant technical field, or equivalent practical experience.
• At least 6+ years of experience in machine learning engineering, with demonstrated success in deploying scalable ML models in a production environment.

Ideal Skills & Experience:

• Deep expertise in one or more of the following areas: machine learning, recommendation systems, pattern recognition, data mining, artificial intelligence, or related technical fields.
• Proven track record of developing machine learning models from inception to business impact, demonstrating the ability to solve complex challenges with innovative solutions.
• Proficiency with Python is required, and experience with Golang is a plus.
• Demonstrated technical leadership in guiding teams, owning end-to-end projects, and setting the technical direction to achieve project goals efficiently.
• Experience working with relational databases, data warehouses, and using SQL to explore them.
• Strong familiarity with AWS cloud services, especially in deploying and managing machine learning solutions and scaling them in a cost-effective manner.
• Knowledgeable in Kubernetes, Docker, and CI/CD pipelines for efficient deployment and management of ML models.
• Comfortable with monitoring and observability tools tailored for machine learning models (e.g., Prometheus, Grafana, AWS CloudWatch) and experienced in developing recommender systems or enhancing user experiences through personalized recommendations.
• Solid foundation in data processing and pipeline frameworks (e.g., Apache Spark, Kafka) for handling real-time data streams.

About You:

• • You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
  • You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
  • You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
  • You earn trust - you listen attentively, speak candidly, and treat others respectfully.

What Makes Working at Sezzle Awesome:

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-Remote

The salary range for this role is $50,000 - $120,000 per year (Gross in USD) 

About Sezzle:

With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. As we continue to shape the future of fintech and retail, we’re building an innovative, dynamic team passionate about creating more than just a transaction but a truly unique shopping journey. If you’re excited about pushing boundaries in tech and delivering a game-changing experience for consumers and merchants alike, come join us at Sezzle and help create the future of shopping!

About the Role: 

We are seeking a talented and motivated Principal Machine Learning Engineerwho is best in class with a high IQ plus a high EQ. This role presents an exciting opportunity to thrive in a dynamic, fast-paced environment within a rapidly growing team, with abundant prospects for career advancement.

You will be responsible for overseeing the design, development, and deployment of machine learning models that power and enhance our financial platform. In this role, you will drive the creation of scalable machine learning solutions for personalized recommendations in the Sezzle marketplace, fraud detection, and credit risk assessment, utilizing a combination of cloud services, open-source tools, and proprietary algorithms.

Your leadership will be key in blending machine learning development and operations (MLOps) to automate and optimize the full lifecycle of our ML models. You will collaborate with a team of engineers and data scientists to build large-scale, high-quality solutions that address diverse challenges in the shopping and fintech space. You’ll ensure our AI-driven features are robust, efficient, and scalable as we continue to grow.

Responsibilities:

• Design, Build, and Maintain Scalable ML Infrastructure: Lead the design and development of scalable machine learning infrastructure on AWS, utilizing services like AWS Sagemaker for efficient model training and deployment.
• Collaborate with Product Teams: Work closely with product teams to develop MVPs for AI-driven features, ensuring quick iterations and market testing to refine solutions effectively.
• Develop Monitoring & Alerting Frameworks: Create and enhance monitoring and alerting systems for machine learning models to ensure high performance, reliability, and minimal downtime.
• Support Cross-Departmental AI Utilization: Enable various departments within the organization to leverage AI/ML models, including cutting-edge Generative AI solutions, for different use cases.
• Provide Production Support: Offer expertise in debugging and resolving issues related to machine learning models in production, participating in on-call rotations for operational troubleshooting and incident resolution.
• Scale ML Architecture: Design and scale machine learning architecture to support rapid user growth, leveraging deep knowledge of AWS and ML best practices to ensure robustness and efficiency.
• Mentor and Elevate Team Skills: Conduct code reviews, mentor team members, and elevate overall team capabilities through knowledge sharing and collaboration.
• Stay Ahead of the Curve: Stay updated with the latest advancements in machine learning technologies and AWS services, driving the adoption of cutting-edge solutions to maintain a competitive edge.

Minimum Requirements:

• Bachelor's degree in Computer Science, Computer Engineering, Machine Learning, Statistics, Physics, or a relevant technical field, or equivalent practical experience.
• At least 6+ years of experience in machine learning engineering, with demonstrated success in deploying scalable ML models in a production environment.

Ideal Skills & Experience:

• Deep expertise in one or more of the following areas: machine learning, recommendation systems, pattern recognition, data mining, artificial intelligence, or related technical fields.
• Proven track record of developing machine learning models from inception to business impact, demonstrating the ability to solve complex challenges with innovative solutions.
• Proficiency with Python is required, and experience with Golang is a plus.
• Demonstrated technical leadership in guiding teams, owning end-to-end projects, and setting the technical direction to achieve project goals efficiently.
• Experience working with relational databases, data warehouses, and using SQL to explore them.
• Strong familiarity with AWS cloud services, especially in deploying and managing machine learning solutions and scaling them in a cost-effective manner.
• Knowledgeable in Kubernetes, Docker, and CI/CD pipelines for efficient deployment and management of ML models.
• Comfortable with monitoring and observability tools tailored for machine learning models (e.g., Prometheus, Grafana, AWS CloudWatch) and experienced in developing recommender systems or enhancing user experiences through personalized recommendations.
• Solid foundation in data processing and pipeline frameworks (e.g., Apache Spark, Kafka) for handling real-time data streams.

About You:

• • You have relentlessly high standards - many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
  • You’re not bound by convention - your success—and much of the fun—lies in developing new ways to do things
  • You need action - speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
  • You earn trust - you listen attentively, speak candidly, and treat others respectfully.

What Makes Working at Sezzle Awesome:

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire. 

#Li-Remote

Your impact

Handshake is hiring a Technical Lead Manager, Machine Learning with a focus on Generative AI and Recommendations reporting to our Head of Core Relevance. 

AI is the future and we are excited to further invest in providing AI resources for our users on our platform. Is it possible to thoughtfully design a responsible, AI-driven product that can help our students progress from educational aspirations to career achievements?  In this role, you will work on tackling that goal as part of a lean, high-visibility team. You will be responsible for helping advance our AI product and infrastructure vision towards our mission of democratizing opportunity for millions of students on Handshake.

You will be part of a high-impact org that has already built a Data platform housing billions of data points, with cutting-edge production systems such as embedding-based retrieval, Graph Neural Networks, Fine-Tuned LLMs, and multi-stage rankers.  You will level up existing ML systems and drive marketplace metrics, while also accelerating greenfield AI-based products such as Social/Feed.  We’ll do all of this responsibly, with developed workstreams around Explainability, Fairness, and Quality.

Your role

• You will be a Force Multiplier - setting technical direction, shaping engineering culture, identifying and adopting industry best practices, designing effective partnerships across the company, mentoring and coaching direct reports / peers, and more. 
• You will be a Leader-  managing a lean team of machine learning engineers and data scientists while enabling effective collaboration, high-quality execution, and technical excellence across the Data organization
• You will be an Innovator -  developing algorithms and Machine Learning systems that connect users across the Handshake marketplace; from students looking for their first jobs and internships to employers sourcing candidates for high-priority roles.
• You will be a Collaborator -being an effective partner to product managers; you will work with product managers in driving new user experiences through Machine Learning and Natural Language Processing and build experiments that drive key product decisions and provide invaluable insights.

Your experience

You are an experienced, hands-on senior engineering leader with extensive experience identifying problems, coming up with technical solutions, and driving projects to completion. You care about culture, mentorship, and collaboration just as much as you care about coding, architecture, and technical design. You have an extreme user-focus, you are comfortable with ambiguity, you can drive alignment, and you make thoughtful data-driven decisions. 

• Basic Qualifications
  • Bachelor’s degree in Computer Science or related technical field or equivalent technical experience.
  • 7+ years of industry ML experience
  • Experience as Tech Lead or Manger 
• Preferred Qualifications:  
  
  • End-to-End experience building web-scale AI systems, feature stores, microservices
  • Background in one or more of the following areas of machine learning: recommendations, optimization, natural language processing (NLP), deep learning, LLMs, explainable AI
  • Experience building applications atop of IAAS (Google Cloud Platform, Amazon Web Services, Azure Cloud Services, etc.)
  • Experience working directly with cross-functional teams such as product management, analytics, engineering, and design.
  • Excellent communication skills — ability to succinctly communicate results and tell compelling stories with data to an out-of-domain audience (e.g. presenting findings and deep-dives to senior leadership).

Compensation range

• $235,000-$300,000

Want to learn more about what it's like to work at Handshake?Check out these interviews from our team members!