If you have a curious disposition, love helping people learn, and can turn complex software and workflows into clear, engaging learning experiences, keep reading!

Grant Street Group is a growing SaaS provider to public sector clients. Whether it is tax processing or electronic payments, we have tools to make government work better.

We’re looking for a Training Specialist to design, deliver, and continuously improve training for our internal teams and our clients. This person will help define and own an ecosystem of training at GSG: identifying gaps, prioritizing audiences and topics, and measuring the impact of training.

In this role you won’t always be the subject matter expert. Instead, you’ll partner with product, operations, and client-facing teams to synthesize information and turn it into learner-friendly content across formats (live virtual sessions, self-paced modules, micro-learnings, and reference materials).

What you’ll do:

Lead, maintain, and innovate GSG’s training program for internal and external stakeholders with a focus on onboarding, cross-team, implementation, and client training.
Conduct training needs assessments to identify skill and knowledge gaps, then prioritize audiences, topics, and formats based on business goals.
Design learner-centered training that applies adult learning principles, focusing on behavior change and real-world workflows rather than “checking the box.”
Create and curate training content that helps clients and staff learn our products and processes effectively through virtual sessions, self-paced modules, micro-learnings, and reference materials.
Interview subject matter experts and stakeholders, review documentation, and synthesize what you learn into clear, structured training without relying on SMEs to write the content for you.
Deliver engaging live training or train-the-trainer sessions for internal and external audiences as needed.
Leverage our learning tools, including our learning management system (TalentLMS) and other platforms, to organize, publish, and maintain training content.
Measure training effectiveness, using feedback, assessments, and behavioral or performance indicators to evaluate whether training is working and where to iterate.
Build and maintain a training roadmap that makes it easy for teams to see what training exists, what’s coming next, and how training aligns with broader company initiatives.
Partner closely with operations, product, project management, and HR to ensure training is aligned with project milestones, implementation plans, and internal process changes.

What makes you a great fit:

You love learning and ramp up quickly on new technologies and domains, asking great questions when something isn’t clear.
You are skilled at information synthesis—you can pull from conversations, documentation, and live demos, then decide what learners actually need to know and how to present it.
You are a clear, concise writer and communicator who can explain complex topics in simple, approachable language and adapt your style for different audiences.
You sweat the small stuff—you care about structure, flow, visuals, and consistency, and you’re willing to iterate until materials are polished and effective.
You are energized by building programs from the ground up—creating templates, standards, and repeatable practices that make it easier for others to create and deliver great training.
You are comfortable facilitating live sessions, reading the room, and adjusting on the fly based on learner questions and feedback.
You enjoy collaborating across teams and can build strong relationships with busy subject matter experts, leaders, and peers.

We expect an excellent Training Specialist candidate to bring many (but not necessarily all) of the following:

3–7 years of experience in a corporate training, instructional design, learning & development, or similar role, ideally in a software, technology, or complex process environment.
Strong grounding in adult learning principles and experience applying them in course design, facilitation, and evaluation.
Hands-on experience with a learning management system (LMS) (such as TalentLMS or similar), including organizing courses, tracking completion, and reporting on engagement.
Familiarity with content creation tools and basic image/screen capture or video tools.
Proven ability to measure training effectiveness and use data and feedback to iterate on content, delivery methods, and program design.
Excellent verbal and written communication skills, including public speaking, facilitation, and stakeholder communication.
Strong organization and time-management skills, with the ability to manage multiple projects, stakeholders, and deadlines simultaneously.

Nice to have

Demonstrated experience designing and delivering training for software products or complex workflows (e.g., SaaS applications, enterprise tools, or detailed operational processes).
Experience building training programs in a train-the-trainer model or supporting large-scale onboarding/implementation efforts.
Experience with client-facing training (e.g., training external customers or partners on software products or services).
Familiarity with e-learning design (storyboards, interactive modules, quizzes, and assessments) and/or tools used to build self-paced, multimedia content.
Background working with or alongside technical documentation writers, product managers, or business analysts in a software environment.

Why work at Grant Street Group?

We reward teamwork, professional excellence, and individual responsibility. Using the best collaboration tools available, we offer a technology-rich work environment that makes it possible for us to support on-site and telecommuting positions tailored to the needs of our employees.

This is a remote position and may require working across time zones as-needed. We anticipate 10-15% required travel for on-site client trainings and annual company events.

If you are passionate about your work, you have an entrepreneurial spirit, and you want to be on a team of exceptional professionals, then this could be the opportunity you are looking for!

Expected Salary Range: $75,000 – $110,000/year

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Grant Street Group

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Training Specialist