Lead Software Developer

Sorry, this job was removed at 12:28 p.m. (CST) on Saturday, Jul 19, 2025
Chicago, IL
Hybrid
Information Technology • Professional Services • Software • Consulting
We’re an end-to-end custom software development company, offering services across discovery, strategy, design, build.
The Role

Highland is looking for a Lead Developer to lead a key development effort while taking on elements of broader technology leadership over time. 

Title: Lead Software Developer

Location: Chicagoland.  We work together once a week at our Loop offices and at our client’s offices from time to time.  

Hours: We’re based in Chicago and typically work 9am–5pm CST. There is some flexibility here. 

Travel: Overnight travel up to 10%.

Please note this is a three month contract to hire position based in Chicago.

The Ideal Candidate 

  • Empathetic to user, client, and team needs
  • Has significant experience in consulting as an employee of a consulting agency/firm
  • Has experience consulting with C-level stakeholders in medium to large businesses
  • Motivated by tough problems, both in and out of the code
  • Collaborates with product managers, clients, and other developers to define solutions, create detailed delivery plans, and adjust plans as needed
  • Possesses the ability to create and deliver effective presentations, communicating complex information in a simple manner
  • Proud they don’t let things slip through the cracks
  • Enjoys improving DX (developer experience, like UX for devs)
  • Has experience evaluating legacy code bases with a bias toward improving rather than replacing
  • Has strong, favorable opinions about TDD and pairing/ensemble programming
  • Has high standards for code quality
  • Wants to more deeply learn their tools and tech stack
  • Has experience managing several developers as direct reports
  • You have managed 3rd party vendor partners in areas such as managed services or hosting providers

Development Experience 

  • You have multiple years of experience modernizing legacy applications
  • You can effectively communicate trade-offs to both technical and non-technical team members
  • You have been part of a team that has successfully built several medium-to-large scale applications
  • You have a strong capability in Laravel and at least a working knowledge of client-side MVVM frameworks like Vue and React
  • You have experience estimating complex technical work through analysis and work breakdown
  • You may have experience with:
    • Web application system architecture & design
    • Configuring servers and automating deployments
    • A11y & W3C standards
    • Tailwind CSS
    • Other server-side languages
    • Laravel Livewire

Team & Process 

  • Our project teams include some combination of software engineers, product managers, and direct client involvement. 
  • We’re a curious bunch, continually assessing and improving digital product development practices with product and user-centric thinking. 
  • We seek diverse perspectives for feedback and critique throughout projects and initiatives. 

Client Relationships

  • All of our project team members advise and consult with clients and team members on product and technical direction. We aim to always keep end-user and business outcomes in mind to make the right trade-offs. 
  • We strive to have frank, honest conversations with our clients and team members. 

Education and Experience “Requirements”: 

  • A degree in Computer Science is preferred. Other comparable training is acceptable.
  • Strong technical consulting skills
  • 6+ years of proven experience developing custom software

Compensation & Benefits

  • Three months initial contract to hire period
  • Full-time salary of $135,000 to $160,000 plus annual bonus target $5,000 to $10,000
  • Health, dental and vision insurance
  • 401k retirement savings plan
  • Unlimited sick time, 9 paid company holidays, 4 weeks’ paid time off
  • 40 hours of professional development time and a $1,000 learning stipend each year
  • Fully paid parental leave: 12 weeks for birth mothers or 6 weeks for non-birth parents
  • Short-term and long-term disability insurance and life insurance (Highland pays 100% of the premiums)


 

About Highland 

Highland is a digital product and innovation consultancy based in Chicago. We research, design, and build digital products and experiences for mission-driven organizations and customer-centric companies. Over 25 years, our team of researchers, strategists, designers, and developers has helped organizations launch over 300 digital products, turning their biggest uncertainties into opportunities for growth.

We often refer to what we design as ‘Experiences that Matter’: digital products and experiences that make the world a better place to live in. We primarily work with (1) leaders of mid-market services companies, (2) enterprise leaders within digital, design, and innovation, and (3) leaders at membership associations.

Our mission is rooted in Human Flourishing—inspired by research conducted at Harvard University’s Institute for Quantitative Social Science. We design our work to help human beings flourish, while allowing ourselves to flourish as well. For us, our values—People First, Give a Damn, Be Curious, and Be Transparent—are not just things to hang on the wall, but something we live by every day.

Highland’s Core Values 

People First: What we make and how we work should make it a little bit better to be alive: for us, our clients, and their customers. 

Be Curious: The big picture is everyone's responsibility. There is always more to learn. We are generous in teaching what we know. 

Be Transparent: We're accountable to our clients and to each other, and respond to problems with solutions, not blame. Vulnerability, while risky, leads to trust and understanding. 

Give a Damn: Our clients’ goals are our goals. We do work we can be proud of. Quality is non-negotiable. 

Our Commitment to Diversity and Inclusion 

Highland is committed to creating a just, equitable workplace, and is actively seeking candidates who can bring the value of diverse lived experiences to this position. We look for candidates who have a high level of demonstrated comfort with cultural competency;

women, people of color, people with disabilities, and people who identify as LGBTQ+ are encouraged to apply.

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The Company
HQ: Chicago, IL
30 Employees
Year Founded: 1999

What We Do

At Highland, we create powerful, engaging digital and physical experiences for our clients. We love analyzing, strategizing, optimizing, and building digital solutions and services that help organizations grow and empower those they serve -- whether it’s internal cross-functional teams or external customers and consumers.
Highland is comprised of two service arms that are both in mission to ignite our clients’ vision, accelerate time to launch and time to value, and enable them to succeed now, and in the future.

Highland research, design, and build: We specialize in customer research, digital product design, and custom software development, creating experiences that promote human flourishing and make the world a better place to live in. Some of our clients ask us to help them improve existing digital products and experiences and others bring us inspired ideas about an entirely new thing they want to bring into the world. No matter where they are in their journey, we offer end-to-end services that produce experiences that matter: for us, for our clients, and for their customers.

Highland SaaS delivery: We specialize in designing and optimizing our SaaS software partner solutions (Creatio, monday.com, SugarCRM) to help businesses reach maximum potential across operational efficiency and agility, team collaboration, and customer relationship management. From business process mapping to platform customization and configuration to user training, we take a client-centric approach ensuring we implement software that’s crafted for each business and their unique business needs.

Why Work With Us

We're committed to being a workplace where people can bring their whole selves and work towards a more just and equitable world. We create small, skilled, empowered teams that work hand-in-hand with our clients, guiding them through our proven processes and teaching along the way.

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