by Terrance Ellis | Dec 17, 2025 | Uncategorized
Splitwise Pro is the growth engine, and this role runs the room. If you love leading a small team, shipping experiments fast, and balancing conversion wins with a product that still feels respectful to users, this is a serious opportunity.
About Splitwise
Splitwise helps millions of people share expenses with friends and family so money puts less stress on relationships. Their Pro subscription powers company growth, and the team runs frequent experiments while keeping the codebase reliable, maintainable, and built to scale.
Schedule
- Remote anywhere in the USA, or based in Providence, RI, New York, NY, or Los Angeles, CA
- Flexible hours, with meeting hours generally 10:00am to 5:00pm ET
- Hybrid company with 2–3 off-site gatherings each year
- You’ll manage 3 Ruby on Rails engineers, with potential team growth in 2026
What You’ll Do
• Lead Splitwise Pro Growth by improving Pro features, conversion, and subscription revenue through rapid iteration and A/B testing
• Manage and mentor a small team of engineers while providing architectural guidance and occasional code contributions
• Partner closely with PM, design, data science, and mobile teams to scope, ship, and learn quickly
What You Need
• 8+ years engineering experience and 1+ year as an engineering manager or tech lead
• Strong communication across engineering, product, and data, plus a leadership style that builds psychological safety
• Comfort working in a Ruby on Rails environment (and writing Ruby during interviews), plus a data-informed experimentation mindset
Benefits
• $201,000–$226,000 base salary (depends on experience and tenure) plus equity/stock options
• Top tier health care (100% covered for you, 50% for dependents), plus dental and vision
• Unlimited/flexible PTO, paid parental leave (12+ weeks), and 401(k) with match
If you want real ownership without the burnout culture, this is built for that. Small team, big surface area, and your decisions will show up directly in growth, product quality, and team health.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 17, 2025 | Uncategorized
Splitwise is building for scale, trust, and real life money stress, and their backend is the engine. If you like shipping often, owning systems end to end, and sweating the details that keep millions of users safe and happy, this is that kind of gig.
About Splitwise
Splitwise helps people share expenses with friends and family so money causes less friction in relationships. Backend engineers here are generalists who build public facing features, power the APIs behind the mobile apps, and help scale infrastructure with reliability and security in mind.
Schedule
- Remote anywhere in the USA, or based in Providence, RI, New York, NY, or Los Angeles, CA
- Mid level and above
- Flexible hours, with meeting hours generally 10:00am to 5:00pm ET
- Frequent deploys (often many times per day), with a strong focus on maintainability and backwards compatibility
What You’ll Do
• Build and maintain backend services used by millions of people
• Plan and implement API and architecture updates in a Ruby on Rails codebase
• Monitor production health and support reliability, performance, and scaling efforts
What You Need
• Ability to write clean, testable, maintainable code and communicate clearly about technical decisions
• Strong debugging instincts and a “let’s figure out what broke” mindset
• Familiarity with Ruby and/or Ruby on Rails (or willingness to ramp fast, including writing Ruby during interviews)
Benefits
• $162,000–$216,500 base salary (depends on experience and tenure) plus equity/stock options
• Top tier health care (100% covered for you, 50% for dependents), plus dental and vision
• Unlimited/flexible PTO, paid parental leave (12+ weeks), and 401(k) with match
Roles like this don’t come with training wheels, but they do come with real impact. If you want to help Splitwise scale toward 100 million+ users and still ship like a small team, shoot your shot.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 16, 2025 | Uncategorized
Be the technical glue between Housecall Pro and its biggest partners. If you’re equal parts customer-obsessed and technically curious, and you love turning messy integration needs into clear requirements and real solutions, this role is a strong fit.
About Housecall Pro
Housecall Pro helps home service professionals streamline scheduling, dispatching, payments, and more so they can grow and get time back. Founded in 2013, they support 40,000+ businesses and build tools that help Pros run better operations and live well.
Schedule
Full-time, remote (#LI-Remote). Travel required as needed, typically 15–30% annually (with seasonal variation). Location-based compensation.
What You’ll Do
⦁ Lead discovery sessions to understand partner business requirements and technical needs
⦁ Run partner calls and demos to showcase product capabilities
⦁ Document gap analyses, integration requirements, and scope of work
⦁ Create clear requirement documents that translate partner needs into actionable work
⦁ Collaborate with engineering on API integrations and technical solutions
⦁ Partner with product management to prioritize partner-specific features and requests
⦁ Coordinate with account management to ensure a seamless partner experience
⦁ Work with legal and business development on contract requirements and product exhibits
⦁ Drive onboarding and pilot implementations, tracking progress through rollout
⦁ Troubleshoot technical issues, provide workarounds, and handle escalations
⦁ Facilitate partner training and onboarding sessions
⦁ Build repeatable processes: SOPs, playbooks, escalation workflows, and communication protocols
⦁ Manage product request backlogs and prioritization frameworks, spotting patterns across partners
What You Need
⦁ 3–5+ years in technical account management, customer success, product management, or product operations
⦁ Bachelor’s degree in a related field or equivalent work experience
⦁ Experience with enterprise software integrations and APIs
⦁ Experience using AI tooling/optimization to improve efficiency and operational workflows
⦁ Strong understanding of SaaS business models and enterprise operations
⦁ Proven ability to manage complex, multi-stakeholder projects
⦁ Strong communication skills, including presenting to executive audiences
⦁ Organized, analytical, and confident balancing partner advocacy with business priorities
Benefits
⦁ Medical, dental, vision, life, and disability coverage plus 401(k)
⦁ Paid holidays and flexible, take-it-as-you-need-it PTO
⦁ Equity eligibility in a rapidly growing startup backed by top-tier VCs
⦁ Monthly tech reimbursements
⦁ Paid parental leave and employee assistance program
⦁ Compensation range: $96,000–$120,000 (location-based, plus equity eligibility)
This is a high-impact seat: you’re not just “supporting” partnerships, you’re shaping how they succeed and scale.
If you’re the type who can translate business goals into technical execution without losing either side, go get it.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 16, 2025 | Uncategorized
Own the AI product vision that drives growth, and turn Housecall Pro’s customer data into real outcomes for small businesses. If you can lead strategy and execution, build AI-first products responsibly, and ship fast with quality guardrails, this role is calling your name.
About Housecall Pro
Housecall Pro helps home service professionals streamline scheduling, dispatching, payments, and more so they can grow and get time back. Founded in 2013, they support 40,000+ businesses with a mission to champion Pros to success through practical, high-impact technology.
Schedule
Full-time, remote (#LI-Remote). Work cross-functionally with engineering, design, analytics, and go-to-market partners across time zones.
What You’ll Do
⦁ Lead end-to-end product strategy and execution for two flagship offerings: Marketing AI and Sales AI
⦁ Define crisp problems and outcome-based roadmaps that drive measurable business impact
⦁ Build probabilistic AI experiences with guardrails, feedback loops, and high-quality user outcomes
⦁ Champion AI-native product development methods: rapid prototyping, evaluations, and fast iteration cycles
⦁ Manage and prioritize roadmaps, resources, and timelines across teams to maximize impact
⦁ Partner across marketing, sales, customer success, and ops to launch, support, and scale AI solutions
⦁ Establish KPIs, monitor performance, and drive continuous improvement using data-driven insight
⦁ Lead and mentor product managers, building a culture of ownership, innovation, and continuous learning
⦁ Identify future AI opportunities and fold them into long-term planning and platform strategy
What You Need
⦁ Proven experience building and launching AI-first or AI-powered products end-to-end
⦁ Fluency in AI product methodologies (rapid prototyping, evaluations, data ingestion pipelines)
⦁ 12+ years of product management experience (SaaS preferred)
⦁ 7+ years of product leadership experience with direct people management
⦁ Track record of shipping scalable products with measurable business impact
⦁ Strong strategic thinking with the ability to switch between vision and day-to-day execution
⦁ Experience defining KPIs and iterating based on performance data
⦁ Excellent cross-functional leadership and stakeholder alignment skills
⦁ Bachelor’s degree or equivalent work experience
Benefits
⦁ Medical, dental, vision, life, and disability coverage plus 401(k)
⦁ Paid holidays and flexible, take-it-as-you-need-it PTO
⦁ Equity in a rapidly growing startup backed by top-tier VCs
⦁ Monthly tech reimbursements
⦁ Paid parental leave and employee assistance program
⦁ Compensation range: $168,000–$198,000 + 10% variable bonus (plus equity eligibility)
They’re scaling their AI practice and want a leader who can ship responsibly, inspire a team, and turn data into durable customer value.
If you’ve built AI products that actually move the needle, this is a seat with real leverage.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 16, 2025 | Uncategorized
This is the “architect of architects” role. You’ll set the technical vision that moves Housecall Pro from boardroom priorities to real-world platform outcomes, including enterprise readiness, compliance, and AI integrations, all while modernizing core services at scale.
About Housecall Pro
Housecall Pro helps home service professionals streamline scheduling, dispatching, payments, and more so they can save time, grow profitably, and live well. Founded in 2013, they support 40,000+ businesses with a mission to champion Pros through reliable, scalable technology.
Schedule
Full-time, remote (#LI-Remote). Location-based compensation. You’ll partner closely with senior leadership and cross-functional engineering teams across multiple domains.
What You’ll Do
⦁ Define and evolve platform architecture that enables enterprise scale and increases developer velocity
⦁ Establish patterns, platform standards, and reusable primitives adopted across engineering teams
⦁ Partner with senior leaders to translate business priorities (enterprise readiness, AI integrations, compliance) into architectural strategy and execution
⦁ Lead cross-functional design reviews and guide major technical decisions for company-wide initiatives
⦁ Identify and reduce technical debt, system bottlenecks, and architectural friction across domains
⦁ Mentor senior engineers and help embed platform thinking, excellence, and strong engineering culture
⦁ Contribute hands-on when needed to model secure, scalable foundational components
⦁ Drive best practices through architecture docs, tech talks, and internal training
⦁ Evaluate and integrate emerging technologies that improve reliability, performance, and maintainability
What You Need
⦁ 15+ years of software engineering experience designing distributed, cloud-based systems
⦁ Deep platform expertise across services like payments, billing, identity, data, and APIs
⦁ Track record of delivering large-scale systems and influencing across organizational boundaries
⦁ Proven experience establishing architectural strategies and patterns that scale across teams
⦁ Proficiency across multiple languages/frameworks (Ruby, React, JavaScript, Python, Java, Node.js, etc.)
⦁ Strong command of modern methodologies and tooling (Agile/Scrum, CI/CD, observability)
⦁ Bachelor’s degree in CS/Engineering (or equivalent practical experience)
⦁ Strong “lead without authority” skill set and the ability to guide teams through ambiguity
Benefits
⦁ Medical, dental, vision, life, and disability coverage plus 401(k)
⦁ Paid holidays and flexible, take-it-as-you-need-it PTO
⦁ Equity in a rapidly growing startup backed by top-tier VCs
⦁ Monthly tech reimbursements
⦁ Paid parental leave and employee assistance program
⦁ Compensation range: $216,000–$270,000 (plus equity eligibility)
This is a rare seat at the table, with real leverage across systems, culture, and long-term platform direction.
If you’ve been waiting for a role where your architecture decisions truly shape the company, this is it.
Happy Hunting,
~Two Chicks…
