Lead Business Systems Analyst / Team Lead

Job Posting / May 2021

Gain Compliance is developing innovative software products to help insurance professionals with the burden of their compliance-related filings. We are a team who is passionate about building great products that customers love!

We are looking for a Lead Analyst with critical judgment and attention to detail to lead a team of analysts and assist in the development, maintenance, and testing of the configurations that drive our world-class software products.

You’ll be Doing:

  • Work closely with Senior Management to collaborate on strategy to meet company goals.
  • Collaborate closely with the Client Services, Product, and Engineering teams in planning and execution of strategic objectives.
  • Lead a high-performing team of analysts responsible for the development and support of product configurations that drive our world-class software products.
  • Coordinate the planning, prioritization, and timeline of work tied to meeting company and team goals while closely tracking and communicating around the complex network of dependencies (and potential blockers) for that work and how it impacts your team and other teams across the organization.
  • Engage the team and build one-mindedness around the planning and execution of company goals.
  • Become a subject matter expert and leader in our business, product, and the voice of our customers.
  • Lead by example, taking a senior role in the day to day work of the team.
  • Provide guidance and leadership in the implementation and maintenance of processes and systems to mature the operations of the team (and our work in general).
  • Provide guidance, instruction, training, and leadership to help your team excel.
  • Coach and enable team members to reach their full potential.
  • Empower team members with skills to improve their confidence, product knowledge, and communication skills.
  • Develop a humble, fun-loving, and highly communicative and collaborative team culture.
  • Develop key milestones for the team and lead the execution of team initiatives.
  • Contribute to the growth of the company by helping the team succeed and meet team goals.
  • Foster a pleasant working environment that inspires the team.
  • Enjoy seeing your co-workers’ pets and children on video calls.
  • Assist with other tasks that arise in the context of a fast-paced technology startup
  • As part of a growing company, all employees wear multiple hats and contribute to the success of our company in multiple ways.

What You’ll Bring:

  • Ability to quickly pick up projects and own them to completion.
  • A high degree of motivation and the ability to exercise critical judgment and reasoning.
  • An analytical, questioning, and systems-oriented thought process backed by real-life experiences that challenge the status quo and bring new, winning solutions that help mature the organization and organizational practices as a whole (expand our solution spaces help us think new and better in all we do!).
  • Passion to deliver value for the customer experience.
  • Strong technical aptitude, with competency in using Google Productivity Suite and/or Microsoft Word, Excel, PowerPoint, and other software products.
  • Outstanding project management, follow-through and attention to details.
  • A growth mindset, intellectual curiosity, and eagerness to contribute.
  • Comfort working on a distributed team and using chat, video calls and document writing to champion and communicate your ideas (sometimes through silly gifs).
  • Self motivation to have an outsized impact with minimal oversight.
  • Ability to see the big picture and make connections based on daily operations.


  • SaaS software experience.
  • Insurance industry experience.
  • Accounting, financial reporting, or statutory financial statement experience.
  • Minimum 2 year degree or equivalent with an emphasis in Accounting and or Management Information Systems (MIS).

We are a small startup with a lot of opportunities and minimal boundaries. You will have a direct and visible impact on the success of the company and you will be rewarded with (appreciation and) with opportunities to match your contribution. If this excites you please apply at careers@gaincompliance.com and attach a resume and cover letter explaining why you’re the perfect person to help us.

The company is located in the East Village of Des Moines, Iowa. You’ll work alongside talented, friendly, nerdy, and motivated teammates. You can expect to be highly collaborative with other teams focused on helping our customers thrive.

In addition to the satisfaction (and upside) of joining a successful company in its early stages, we offer a flexible work environment and top-tier benefits.