by Terrance Ellis | Dec 17, 2025 | Uncategorized
This one is the “keep the plane in the sky while we upgrade the engines” job. If you’re the kind of engineer who likes owning EKS end-to-end, standardizing how teams ship across clusters, and being the calm adult in the room when prod acts up, this is your lane.
About Dutchie
Dutchie powers dispensary operations and consumer access across 40+ cannabis markets in the U.S. and Canada. It’s high-volume, regulated, and infrastructure-heavy in the ways that actually matter.
Schedule
- Remote
- Senior ownership + cross-team influence
- You’ll be a “platform multiplier,” not a ticket-taker
What You’ll Do
⦁ Own and evolve EKS across multiple clusters (reliability, security, scalability)
⦁ Standardize multi-cluster deployment patterns and best practices
⦁ Serve as cloud infrastructure SME, guiding teams on decisions and tradeoffs
⦁ Mentor engineers on Kubernetes, AWS, and cloud-native patterns
⦁ Build infra that balances performance, cost, and security
⦁ Partner with dev teams to improve deployment + operations workflows
⦁ Maintain infrastructure-as-code (Pulumi/Terraform) for reproducibility
⦁ Implement cloud security best practices (network policies, IAM, compliance)
What You Need
⦁ Deep Kubernetes experience, specifically production EKS at scale
⦁ Strong AWS fundamentals: EKS, IAM, VPCs, security groups, networking
⦁ Solid Linux troubleshooting + performance tuning
⦁ Docker + orchestration patterns
⦁ IaC with Pulumi or Terraform
⦁ Python or Go for automation/tooling (production-quality)
⦁ Security-first mindset
⦁ 5+ years cloud infrastructure/platform experience (degree or equivalent)
Bonus Points
⦁ Service mesh (Linkerd/Istio)
⦁ GitOps (ArgoCD/Flux)
⦁ Cloudflare (Workers especially)
⦁ Observability (Datadog/Prometheus/Grafana)
⦁ Cost optimization wins
⦁ Open source in cloud-native land
Benefits
⦁ Target salary range: $149,000–$200,000
⦁ Medical, dental, vision
⦁ Stock options
⦁ Tech allowance
⦁ Flexible vacation and sick days
Backbone note: the sneaky “interview winner” here is a story where you reduced toil and standardized deployments (think Helm/Kustomize patterns, GitOps rollout rules, multi-cluster strategy), plus a security/cost win you can quantify. If your resume reads like “I used Kubernetes,” you’re toast. If it reads like “I led a multi-cluster standardization that cut deploy failures 40% and shaved $X/month,” you’re dangerous.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 17, 2025 | Uncategorized
This one’s for a real front-end grownup: React + TypeScript at scale, performance, accessibility, and shipping fast without turning the codebase into a haunted house. If your happy place is clean UI architecture and “delightful but reliable,” Dutchie’s speaking your language.
About Dutchie
Dutchie powers dispensary operations and consumer access across 40+ cannabis markets in the U.S. and Canada. They’re building tools that operate in a heavily regulated space, at big volume, with real-world consequences.
Schedule
- Remote
- Fast-paced product environment (ship often)
- Senior-level ownership across features and quality
What You’ll Do
⦁ Build and maintain core front-end apps using React + TypeScript
⦁ Work with React Query, Redux, Apollo GraphQL, and Styled Components
⦁ Design and ship new features, plus improve existing ones
⦁ Integrate front-end apps with backend APIs for data-driven UI
⦁ Optimize performance, accessibility, and cross-browser compatibility
⦁ Stay current on modern front-end best practices and drive improvements
What You Need
⦁ 5+ years of web/software development experience
⦁ Deep knowledge of JavaScript (ES6+), React, TypeScript, React Query, Redux
⦁ Strong engineering habits: clean, tested, organized code
⦁ Self-starter who can take a project from “we should” to “shipped”
⦁ Strong written/verbal communication and comfort in a quick-moving team
Nice to Have
⦁ Experience in ecommerce, cannabis, or regulated industries
⦁ Open-source contributions
⦁ Remote/distributed team experience
⦁ Enjoys modern tooling and staying sharp
Benefits
⦁ Target salary range: $149,000–$200,000
⦁ Medical, dental, vision
⦁ Stock options
⦁ Tech allowance
⦁ Flexible vacation and sick days
My blunt take: if your resume doesn’t show measurable front-end impact (performance wins, accessibility work, component/system thinking, GraphQL integration, “reduced bugs by X,” “cut load time by Y”), you’ll blend in with the other React folks. Lead with outcomes, not a list of libraries.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 17, 2025 | Uncategorized
This is a real-deal platform role: you’re not just “keeping the lights on,” you’re improving how every engineer at Dutchie ships code. If you love developer experience, CI/CD, Kubernetes, and building tools that make teams faster and safer, this is your playground.
About Dutchie
Dutchie powers dispensary operations and consumer ecommerce across 40+ cannabis markets in the U.S. and Canada. They’re mission-driven around access, social justice, and community impact, and they operate at real scale.
Schedule
- Remote
- Senior-level, cross-functional platform ownership (developer tooling + production infrastructure)
- You’ll partner with engineering leadership and multiple teams regularly
What You’ll Do
⦁ Lead the vision for developer experience and remove friction across the SDLC
⦁ Build and maintain internal tooling from local dev to production workflows
⦁ Improve CI/CD pipelines: speed, safety, reliability, testing workflows
⦁ Help operate and evolve Kubernetes infrastructure (AWS EKS): configs, observability, cost optimization
⦁ Manage AWS infrastructure via IaC (Pulumi and/or Terraform)
⦁ Improve networking and edge reliability using tools like Cloudflare and ingress solutions
What You Need
⦁ 5+ years designing, deploying, and maintaining cloud infrastructure/compute platforms
⦁ Strong Docker + Linux chops (comfortable in shell, optimizing Dockerfiles)
⦁ Deep CI/CD experience (GitHub Actions, GitLab CI, CircleCI, etc.)
⦁ Kubernetes fluency (EKS preferred) with production troubleshooting skills
⦁ IaC experience (Pulumi or Terraform)
⦁ Strong coding skills in Python (preferred), Go, or Ruby
⦁ “Shift-left” mindset for quality, security, and reliability
⦁ Clear communicator who can influence across teams
Benefits
⦁ Target salary range: $149,000–$200,000
⦁ Medical, dental, vision
⦁ Stock options
⦁ Tech allowance (hardware, software, learning resources)
⦁ Flexible vacation and sick time
Straight talk: this role will sniff out “I’ve clicked around Kubernetes” vs “I’ve run prod and built guardrails.” Your resume needs to show impact like: reduced build times, improved deploy safety, standardized dev environments, incident reduction, cost savings, observability wins.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 17, 2025 | Uncategorized
Xenara is Trader Interactive’s newly launched in-house media agency, built to deliver custom, high-impact digital media solutions beyond cookie-cutter packages. If you’re a strategist, planner, creative, or analytics mind who wants “startup energy with real company stability,” this is an open door to multiple media roles.
About Trader Interactive (Xenara)
Xenara is an extension of TI Media, designed to blend strategy, creativity, and data-driven insights into tailored digital advertising and brand solutions. It’s positioned as a new, innovation-forward team inside an established organization, with opportunities spanning media planning, content strategy, digital advertising, and analytics.
Schedule
- Remote (Canada and North America)
- Open-ended “talent pipeline” posting (you’re submitting for matching opportunities, not one fixed role)
- Collaboration across strategy, creative, and performance teams
What You’ll Do
• Help design and execute custom digital media strategies that align to client goals
• Contribute to planning, content strategy, digital advertising, and performance optimization depending on your specialty
• Use insights and data to improve results and strengthen how campaigns are positioned and reported
What You Need
• Experience or strong interest in digital media, advertising, brand strategy, content strategy, media planning, or analytics
• A collaborative mindset and comfort working in a fast-moving environment where processes are still being built
• A portfolio, campaign examples, or measurable results you can speak to (even if it’s from school, freelance, or side projects)
Benefits
• “Best of both worlds” setup: startup-style growth inside a stable, established company
• Remote flexibility across North America/Canada
• Variety of work that goes beyond standard media packages into more customized strategy
Real talk: because this is a general “opportunities” posting, your resume needs to tell them exactly what lane you’re in. Don’t make them guess.
Happy Hunting,
~Two Chicks…
by Terrance Ellis | Dec 17, 2025 | Uncategorized
Splitwise makes high-stakes product decisions with data, not vibes, and this role sits right at that table. If you like turning messy real-world behavior into clear recommendations, building dashboards people actually use, and running experiments that shape what ships next, you’ll fit right in.
About Splitwise
Splitwise helps tens of millions of people share expenses with friends and family so money causes less stress in relationships. It’s a large consumer app with millions of interactions per day, and the data team helps guide product strategy, experimentation, and long-term growth with rigorous analysis.
Schedule
- Remote anywhere in the USA, or based in Providence, RI, New York, NY, or San Francisco, CA
- Flexible hours, with meeting hours generally 10:00am to 5:00pm ET
- Cross-functional collaboration with product, engineering, design, and business teams
- Work spans product analytics, experimentation, business intelligence, and statistical modeling
What You’ll Do
• Design, run, and analyze experiments (A/B tests and similar) to measure product impact
• Define and maintain core metrics, dashboards, and reporting that teams rely on every day
• Use SQL and Python to answer open-ended questions and turn ambiguity into structured analysis and recommendations
What You Need
• Strong quantitative skills, solid statistics foundation, and comfort being transparent about uncertainty
• Ability to write SQL for large datasets and use Python (or similar) for analysis and visualization
• Strong communication skills to translate findings into decisions with product, engineering, and business partners
Benefits
• $130,500–$184,000 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 a role where your analysis changes what gets built and how the business grows, Splitwise is built for that. You’ll have real ownership, real scale, and a team that actually cares about getting the story right.
Happy Hunting,
~Two Chicks…
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…
