Staff Software Engineer, Revenue Systems
Squarespace
Headquarters: New York City; Remote
Squarespace is seeking a talented Staff Software Engineer to support and evolve the systems at the core core of our monetization platform: billing, payments and orders. In this role, you will provide technical oversight over the critical monetization machinery that accepts orders, processes payments and bills subscriptions. You will regularly collaborate with engineering leadership and key product, strategy and finance stakeholders to align technical strategy with Squarespace’s business objectives. This is an opportunity to take on IC technical leadership responsibilities and own system architecture for high-visibility initiatives tied directly to Squarespace's core businesses.
This role is open to remote or hybrid working from our NYC office 3 days per week. You will report to the Director of Revenue Systems.
You'll Get To...
- Own system architectural vision and design for critical areas of our business.
- Transform high-level system vision into estimated project plans for initiatives central to Squarespace’s strategy.
- Serve as technical lead and cross-functional liaison on business-critical projects, making and defending engineering decisions key to the success of the business.
- Mentor engineers on the team to deliver ever greater quality with ever growing autonomy.
- Drive best practices for engineering excellence and technical leadership, influence design reviews, question assumptions, point out pitfalls and foster shared understanding
- Set the engineering quality bar for the team through regular, high-quality code contributions across billing, orders and payments.
Who We're Looking For
- 10 or more years experience specifying, delivering and maintaining complex distributed backend services.
- Significant experience with multiple programming languages (especially Java) and a broad range of tools like Springboot, hibernate, databases, etc.
- Demonstrated experience leading system architecture decisions across multiple teams or initiatives
- Proven ability to serve as a technical lead on cross-functional projects, aligning engineering and business goals without sacrificing engineering quality
- Experience working with billing, orders or payment systems at scale
Benefits & Perks
- A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
- Supplemental Life and Disability Insurance plans
- Fertility and adoption benefits
- Headspace mindfulness app subscription
- Global Employee Assistance Program
- Retirement benefits with employer match
- Flexible paid time off
- 12 weeks paid parental leave and family care leave
- Pretax commuter benefit
- Education reimbursement
- Employee donation match to community organizations
- 7 Global Employee Resource Groups (ERGs)
- Dog-friendly workplace
- Free lunch and snacks
- Private rooftop
- Hack week twice per year
Cash Compensation Range: $170,000 - $299,000 USD
The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.
In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.
About Squarespace
Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.
Our Commitment
Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.
#LI-Hybrid
#LI-Remote
Thank you in advance for providing the following details about your work history from your resume! This helps us ensure that your candidate information is accurate and consistent during the hiring process.
Squarespace will never solicit your personal banking information or ask you to transfer money in connection with a job offer or interview. We also will not reach out to you via phone or SMS without your permission or knowledge.
If you plan to use AI in any capacity during your candidate journey, please review our Candidate AI Policy.
To apply: https://weworkremotely.com/remote-jobs/squarespace-staff-software-engineer-revenue-systems
AI Experience Engineer (Conversational AI)
Upgrade
Headquarters: Canada (Remote)
About the Role:
An AI Experience Engineer owns the full lifecycle of the journeys our customers have with Upgrade's AI agent on chat, voice and email: creation, optimization, edge case handling and containment growth. They build journeys in Sierra's no-code tooling, partner with Upgrade's product groups to bring their servicing flows to the agent, and are accountable for whether the agent resolves the customer's issue safely, accurately and without a human.
We are hiring an AI Experience Engineer to own Upgrade's customer-facing AI agent. You will sit between engineering, product and customer operations. You will turn servicing workflows, such as making a payment, checking loan details, updating an address or enabling autopay, into production journeys and keep improving them after launch. You will build and own the journeys end to end, from first draft to steady state. The work is part builder, part analyst: design the flow, handle the edge cases, read the transcripts, and keep raising containment. Containment, CSAT, transfer quality and hallucination rate are your metrics.
Within your first year, you will own a portfolio of journeys across products (Personal Loans, Card, BNPL, HELOC, Deposits) and help set the standards for how Upgrade builds, tests and ships AI experiences.
Our Core Technologies
Sierra Agent Studio (no-code journeys), Sierra simulations and conversation analytics, GraphQL and REST APIs (as journey tools), Genesys (contact center handoff), SumoLogic, Grafana, SQL, Javascript/Typescript, Claude and other LLM tools.
What You'll Do
• Journey creation: Design and build Sierra journeys in Agent Studio for chat, voice and email, from discovery with operations through production rollout
• Optimization: Review transcripts, recordings and analytics every week, find where conversations fail or transfer, and ship fixes to journey logic, instructions and knowledge
• Edge case handling: Map the unhappy paths (failed payments, mismatched identity, delinquent accounts, unsupported requests) and make sure each ends in a correct answer or a clean handoff
• Containment: Own containment and CSAT targets per journey, run staged rollouts (1% → 100%), and prioritize the work that moves those numbers most
• Product partnership: Work with product groups (Personal Loans, Card, BNPL, Deposits) to scope new journeys, keep journeys current as products change, and define the APIs the agent needs
• Safety and compliance: Apply tiered authentication and step-up verification, verbatim compliance language and guardrails against hallucination and off-policy answers
• Handoffs: Design transfers to human agents in Genesys with accurate summaries and auth context
• Testing: Build simulation and regression suites so every journey change ships with evidence it did not break existing behavior
• Monitoring: Watch latency, errors and drop-offs in SumoLogic and Grafana, and own the alerts
• Voice tuning: Latency, filler phrases, interruptions, personality and tone
• Sierra relationship: Be the technical owner on our side, escalate platform issues and shape roadmap asks
What We Look For:
• 3–5 years of Frontend Software Engineering experience, or equivalent experience in Solutions Engineering, Conversational AI or Technical Product roles
• Working knowledge of how LLM agents behave: instructions, tool calls, knowledge retrieval, and where each one fails
• Experience building evaluations for non-deterministic systems: test sets, simulations, LLM-as-judge, regression gates
• Enough technical depth to read API specs, work with backend engineers on REST and GraphQL integrations, and reason about authorization and permission scopes
• Working knowledge of JavaScript/TypeScript, with the ability to build and maintain coded journeys and integrate APIs within conversational AI platforms.
• Product and customer mindset: you understand ops procedures, you read transcripts, care about tone, and measure success by whether the customer's problem got solved
• Ownership in production: rollouts, monitoring, log analysis and incident response
• Clear writing and the ability to work with non-engineers in operations, compliance and legal
Nice To Have:
• Hands-on experience with Sierra Agent Studio, or a comparable no-code agent platform (Decagon, Ada, Kore.ai, Google CCAI, Amazon Lex/Connect)
• Voice AI experience: speech-to-text, text-to-speech, latency tuning, barge-in handling
• Contact center systems such as Genesys, and agent handoff design
• Background in fintech or another regulated industry (UDAAP, FDCPA, TCPA, PCI, SOC 2)
• Conversation design or UX writing experience
What We Offer You:
• Competitive salary ($140K-$180K CAN) and stock option plan
• Paid coverage of medical, dental and vision insurance
• Flexible PTO
• Opportunities for professional growth and development
• Paid parental leave
• Health & wellness initiatives
To apply: https://weworkremotely.com/remote-jobs/upgrade-ai-experience-engineer-conversational-ai
Senior Java Developer
Twikey
Headquarters: Ghent - Belgium
URL: https://www.twikey.com/jobs
Are you a driven back-end developer who doesn't wait for instructions, but is already thinking two steps ahead? Who experiments with new technologies and smart solutions alongside the job? Then we want to talk to you.
Straight forward but clear: Twikey isn't looking for someone to just execute. We're looking for someone who thinks, does and keeps going when the going gets tough.
Because fintech is evolving at breakneck speed. That calls for real ownership and for someone who can dive deep on the technical side to keep innovating and improving our platform. You get plenty in return, such as the freedom and responsibility to deliver your own projects. Thanks in part to our organisational structure, you can shape your ideas in the short term and see the results of your hard work quickly.
Driven by your passion for building scalable, performant and secure back-end systems, you continuously raise the bar for your own skills and for our product.
As a member of our development team you work closely with our CTO, 3 fellow developers and 2 testers on the core of our software application. A small, strong team in which you take on a role with real impact on the future of our product.
- You focus on developing and improving the back-end of our platform, optimising the architecture and data processing while keeping the security and stability of our system in mind. This lets you put your technical skills to full use and come up with innovative solutions.
- With your expertise you'll make valuable suggestions and streamline processes for all our stakeholders, so we can work more efficiently and achieve better results.
- You provide technical support on integration projects with software houses, banks and large companies, solving complex technical problems. That gives you the chance to work on challenging projects and to get in touch with a wide range of technologies and industries.
Once you know our product inside out, there are plenty of challenging projects for you to help build.
What are we looking for in you?
- You are driven, curious and enterprising. Not only in your job, but outside of it too. You have a pro-active attitude and are always a few steps ahead: you spot opportunities, grab them and get to work.
- Technical challenges? You take them on, not because you have to, but because you want to learn. You're a self-starter and quickly get to grips with new technologies, languages or frameworks.
- You understand that a good product is never "finished". You draw energy from that mix of creating and fine-tuning. You think along, question things and keep building new solutions.
- You have experience using AI tools to build integrations. You're actively exploring how AI can contribute to smarter user experiences and more efficient software development. Experience with data analytics is an asset.
- You therefore attach a lot of importance to the security, stability and reliability of a system and know what it takes to get there. You work in a structured, meticulous way and write code that is clean, reusable and easy to test.
- You have demonstrable experience with Java, Go and the Spring framework. Experience with API integrations, web services, Linux or other relevant areas is a plus.
- You have a deep understanding of databases. You don't just know how to use them, you know how they work. You have an opinion on structured, high-quality code, architecture and back-end technologies.
- You have a very good command of English, for smooth collaboration with all colleagues and stakeholders. Dutch is an asset.
- You are based in a time zone within one hour of CET, so your working day overlaps with the team's for the daily stand-ups and close day-to-day collaboration.
- You can work independently and enjoy a small team where switching gears quickly, collaboration and knowledge sharing are central.
Twikey offers you:
- An environment where challenge, innovation and autonomy come first.
- The room to experiment, to challenge and to improve. And we expect you to really take that room.
- An ideal setting if you want to grow fast and healthily, both technically and personally. Training, ownership, taking on new or additional roles based on your talents and interests, ... a lot is possible here, and you're at the wheel!
- A complementary team of more than 35 colleagues who move forward together in a respectful and open atmosphere.
- A motivating workplace with plenty of knowledge and expertise, shared both formally during the daily stand-ups and the weekly Friday call, and informally at the coffee machine.
- Appreciation, openness and critical dialogue. Our Friction Hunter Trophy is an example: every month we celebrate the colleague who made the biggest difference for customers, teammates or internally. Your impact gets noticed!
- A modern workplace with different zones (conference, connect, co-work, concentrate) in a recently built, industrial-style office building. Easy to reach by car, by bike and by public transport on the edge of Ghent, right next to the KBC tower.
- A salary package tailored to your experience and skills, with plenty of extra-legal benefits, a collective bonus system and a cafeteria plan to convert your 13th month as you choose.
- The chance to work in an innovative Belgian fintech scale-up that is active in several countries, in a sector that is growing fast!
A job ad doesn't tell you everything. Our colleagues tell you here what it's really like to work at Twikey.
To apply: https://weworkremotely.com/remote-jobs/twikey-senior-java-developer