Senior Software Engineer - WatchTower

About WatchTower

We build technology that powers insurance companies and brokers to be smarter, faster and more reliable. We enable employers to provide protection that employees and their families can depend on. We are WatchTower.

Founded to transform the B2B side of the employee benefits insurance industry from a disparate set of closed systems to a more open and integrated environment, weimagine a future where the industry is connected and facilitated by software instead of bottlenecked by manual processes.

Our founding team has 35+ years of industry experience. We have spent the last two years building the foundation of this business. We've been testing assumptions, developing product, and earning (paying) customers. We recently raised capital to expand our team beyond the founding members. There's much work to do, and you'll be joining at an exciting time with substantial momentum.

Position Overview

Customer demand has surpassed the functionality, and scalability, of the initial proof-of-concept product. We have a capable and seasoned team - with a CTO, Engineering Team Lead, and UX Designer already in place - but adding a Senior Engineer to support the growing business has become vital.

As one of the first full time Engineers, your contributions will have a ripple effect. Your development choices will inherently set the precedent for others to follow, and your attitude will help shape the culture.

This will be a role where you should expect to grow into your career. If you're someone who gets excited about the opportunity to contribute at a MeetUp, then you might be a great fit. You don't need to love public speaking, but you should have conviction in your opinions because they're rooted in personal experience.

Our Stack

  • Front-end: Javascript (with React and Redux)
  • Middleware: Ruby (with Rails)
  • Relational Database: ANSI SQL, Postgres
  • Supporting tools: Python, Django
  • AWS platform

The Senior Engineer will be responsible for understanding, helping to manage and improve upon this infrastructure.

What You'll Do

  • Development Strategy - You'll support our Team Lead and our CTO in the full gamut of development strategies. From tool and technology selection to evaluation and return on investment associated with our technical projects.
  • Development Execution - You consider yourself to be a do-er, so your primary responsibilities will be shipping quality, production grade code, but we'll also expect that you come to the table with suggestions and ideas on best practices and standards that will enable consistency, style, and stability of our codebase.
  • Delivery & Testing - You're excited about working in a Test Driven Development environment, because you understand and believe that testing and documentation are important in supporting efficient and re-usable code.
  • R&D - Our platform includes distinct applications for various internal and external stakeholders including managing internal operations, portal tools for our customers, automating document processing, and enabling reporting and analytics for our customers. We value and seek out opportunities to improve our capabilities across these areas. A percentage of your time will be spent on exploring tools and technologies in the following:
  • Machine Learning
  • Information Retrieval
  • Enterprise Application Development and Delivery
  • Mobile Development


  • 5+ years total development experience
  • 3-5 years Ruby on Rails and Javascript (w/ React & Redux) development experience
  • Proficiency in the community standards for Ruby, Rails, and ES6 environments
  • Demonstrate good discipline in producing tested, clear, and efficient software
  • Has previously led, or has demonstrated the capability to lead projects and team members
  • Comfortable working with remote team members
  • Prioritize the customer above all else
  • Nice-to-have-skills:
  • Enterprise application development experience, particularly data-intensive interfaces
  • API development (in additional to integration)
  • Text extraction techniques such as Regular Expressions and Natural Language Processing
  • Note: Familiarity with the insurance industry is not a requirement. We'll teach you the ropes!


  • Competitive salary
  • Stock options
  • Health insurance (company provided)
  • Flexible vacation policy

Where you'll work

  • Our team works in one of the world's top-ranked incubators, 1871.
  • Enjoy unlimited access to 1,000+ learning and development opportunities per year (events, workshops, mentoring sessions).
  • Located in downtown Chicago our office is in the historic Merchandise Mart building.
  • Accessible from the brown/purple line 'El' stop, and a short walk from Metra train stations.
  • While in-person team meetings will be common, you can expect a work-from-home friendly schedule.

Team Values

WatchTower is a values-based organization. Our Team Values are the beliefs that we hold so deeply that they guide our behavior. This isn't just rhetoric. You can see our Team Values in how we how conduct ourselves, how we treat and communicate with others, and how we make decisions - big or small.

We believe that if our team operates around a shared set of values, then we'll collectively grow and be more successful for it. For that reason we're seeking like-motivated candidates who demonstrate the following:

  • Growth mindset - You fundamentally believe that you can improve.
  • Follow through - When you commit to something you feel a personal obligation to deliver on it.
  • Respect for the individual - You show respect for others through your action and communication with them.
  • Passion for the team - Individual talents combine to an exponentially powerful team.
  • Optimism - You know that the future will be better if we work hard. You realize that a lot can be accomplished over the long term.

WatchTower is committed to building an inclusive working environment regardless of gender, sexual orientation, religion, ethnicity, race, education, age, or other personal characteristics. We believe that people do their best work when they can be themselves, and we want to create an environment to enable them to do just that.

See Inside the Office of 1871

1871 is Chicago’s entrepreneurial hub for digital start-ups. With over 75,000 square-feet of facility space and continuing to expand, 1871 provides Chicago based start-ups with space, daily programming and events, connectivity, access to mentors, educational resources, potential investors, and a community of like-minded entrepreneurs. 1871 strives to help its exceptional 250+ start-ups—and their amazing designers, engineers, and entrepreneurs—build a path to successful businesses.

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