Roles
at Breakaway.

Breakaway helps small and medium-sized businesses establish an AI environment their employees can use in everyday work. Our engagements cover tool selection, configuration, connections to company information, usage policies, training, and support after launch.

The AI Implementation Director will lead this business unit. Once a sale closes, you’ll be responsible for delivering the engagement: assigning the right team, managing the work, meeting commitments, and making sure the client is satisfied with the result.

You’ll lead delivery pods consisting of an AI Implementation Lead and one or more AI Implementation Associates. Working with Breakaway leadership, you’ll develop the delivery process and refine it as we learn from each client. This role requires someone who can manage the business while staying close enough to the work to spot problems and help resolve them.

Responsibilities

• Build and maintain the process for sales handoff, discovery, planning, configuration, governance, launch, training, and post-launch support. Set clear standards for deliverables and approvals.
• Help hire, train, and coach implementation leads and associates. Assign pods based on project needs, balance workloads, and arrange specialist support when necessary.
• Oversee schedules, budgets, scope, and staffing across engagements. Address delays and delivery risks early, and make sure changes are agreed upon before additional work begins.
• Establish a consistent approach to client communication. Clients should know where their project stands, what decisions they need to make, and whom to contact for help.
• Manage delivery through Breakaway’s custom client portal. Keep project plans, tasks, documents, decisions, and approvals accurate, and recommend improvements based on how clients and staff use it.
• Review delivery quality, including configurations, information access, documentation, and training. Confirm that completed work meets the agreed requirements.
• Track adoption and customer satisfaction after launch. Resolve concerns, gather candid feedback, and request permission to document strong results through testimonials and case studies.
• Monitor delivery costs, capacity, and rework. Use that information to improve the process and help Breakaway grow without compromising service.

Qualifications

• You’ve led client implementation, professional services, consulting delivery, or a similar operation with responsibility for people, projects, and financial performance. You can describe work your team delivered successfully and explain how your decisions contributed to the outcome.
• We’re looking for experience managing multiple engagements, developing project leaders, and handling difficult client conversations. You should understand how staffing, scope, and delivery decisions affect profitability.
• You’ll also need practical knowledge of business AI tools, company data connections, permissions, and responsible use. You should be comfortable discussing technical questions with specialists and explaining their implications to business owners.
• Experience building a services practice, supporting smaller businesses, or working with Microsoft 365 or Google Workspace is helpful.

What we’ll expect

Projects are delivered on time and within agreed scope. Clients receive a working AI foundation, understand how to use it, and feel supported throughout the engagement. Your team has clear responsibilities, the portal reflects actual progress, and recurring problems lead to changes in how we work.

You’ll have substantial influence over how this business unit operates, who joins the team, and how Breakaway serves its clients.

Breakaway helps small and medium-sized businesses establish a practical foundation for AI. Our engagements include selecting tools, configuring a business AI environment, connecting company information, establishing usage policies, and helping employees use AI in their work.

As an AI Implementation Lead, you’ll manage client engagements from the sales handoff through launch and completion. You’ll turn the agreed scope into a project plan, coordinate delivery, and guide the client through the decisions needed along the way.

You’ll report to the AI Implementation Director and lead a pod with one or more AI Implementation Associates. You’ll be the client’s primary delivery contact, with responsibility for the schedule, quality of work, and day-to-day relationship. You’ll also coordinate with the client’s technical contacts and bring in specialists when needed.

Responsibilities

• Review the sales handoff, confirm the scope and commitments, and run the kickoff. Establish goals, responsibilities, milestones, and how the client will assess the result.
• Conduct discovery with leaders and employees to understand their tools, information sources, workflows, and constraints. Identify practical opportunities for AI based on that work.
• Maintain the project plan in Breakaway’s custom client portal. Keep tasks, owners, deadlines, dependencies, documents, decisions, and approvals current.
• Guide tool-selection analysis and explain recommendations in terms of business fit, usability, cost, information access, and administration.
• Coordinate workspace configuration, account setup, approved data connections, permissions, testing, and governance work.
• Assign work to associates, review their deliverables, and help them develop their skills. Stay involved where the project needs your judgment or direct contribution.
• Run progress meetings and communicate clearly between them. Raise risks promptly and obtain approval for changes to scope, timing, or effort.
• Organize training around employees’ actual tasks. Work with internal AI champions and provide launch and post-launch support.
• Gather client feedback, review adoption and agreed outcomes, and complete the handoff. Share lessons that can improve future engagements.

Qualifications

• You’ve managed client projects through completion in implementation, consulting, customer success, operations, or a related field. You can organize work, coordinate people, and follow through when progress depends on several parties.
• You should have hands-on experience applying AI tools to business tasks and checking whether their outputs are accurate and useful. You’ll need enough technical knowledge to discuss workspaces, connectors, permissions, and configuration with technical contacts.
• Clear writing and confident meeting facilitation are essential. You should be able to explain unfamiliar concepts, ask questions that uncover a problem, and work comfortably with people who have different levels of technical experience.
• We’re also looking for someone who notices details, keeps commitments, and handles setbacks calmly. Experience with Microsoft 365, Google Workspace, employee training, workflow improvement, or SMB consulting is helpful. Relevant results matter more than a particular degree or certification.

What we’ll expect

Your clients understand the plan and know what they need to do next. Your pod completes work that meets agreed requirements, and you address risks before they become avoidable delays. By the end of an engagement, employees can use AI for relevant tasks, and the client has the documentation and support needed to continue.

You’ll work directly with business decision-makers and help refine Breakaway’s approach as you deliver projects.

Breakaway helps small and medium-sized businesses select and configure AI tools, connect company information, establish usage policies, and train employees to use AI in their daily work.

AI Implementation Associates will help deliver these engagements. You’ll join a pod led by an AI Implementation Lead and contribute to discovery, setup, testing, training, and client support. You’ll spend time working directly with clients as well as preparing and completing work behind the scenes.

This role is a good fit for recent college graduates and other early-career candidates with some technical and business experience. We’re looking for people who enjoy talking with customers, learn unfamiliar tools quickly, and take care with the work they’re given.

Responsibilities

• Prepare for client discovery sessions and help organize questionnaire responses, meeting notes, workflow examples, and follow-up questions.
• Talk with clients about their everyday tasks and help develop useful AI examples, prompts, and reusable instructions.
• Assist with approved workspace setup, user onboarding, document organization, and data-connection testing under your implementation lead’s guidance.
• Test configurations and AI workflows against agreed criteria. Record results and flag problems, including inaccurate outputs or inappropriate access to information.
• Update Breakaway’s custom client portal with task progress, meeting notes, documents, questions, and decisions.
• Prepare training materials and quick-reference guides. Help employees practice with examples that relate to their work.
• Participate in client meetings, demonstrations, training sessions, and support office hours. Answer questions you can handle and bring in others when needed.
• Document feedback and recurring questions so the team can improve its instructions, templates, and delivery process.

You’ll be responsible for assigned tasks, with review and guidance from your implementation lead. As your skills develop, you’ll take on smaller workstreams and more direct client responsibility.

Qualifications

• You have some practical experience with technology and business. That may come from internships, coursework, student organizations, employment, volunteer work, or independent projects.
• You should have used AI tools to accomplish something useful and be able to explain how you checked the results. You’ll also need to be comfortable learning software and working with documents, spreadsheets, and collaboration tools.
• Because this role involves regular client contact, we’re looking for someone who communicates clearly, listens carefully, and enjoys helping people. You should be comfortable asking questions and explaining a process to someone who is trying it for the first time.
• Organization and follow-through matter. You’ll need to keep track of your assignments, document your work, and let your lead know when you’re stuck or a deadline is at risk. Good judgment with confidential information is also essential.
• A degree in business, information systems, computer science, engineering, communications, or a related area is helpful; equivalent practical experience is welcome. More important is a deep curiosity about and enthusiasm for AI, along with personal or professional experience using AI tools to solve problems, improve workflows, and create new possibilities. A passion for exploring how these tools work, sharing practical insights, and teaching others is especially valued. Experience with Microsoft 365, Google Workspace, data analysis, basic coding, or workflow automation is a plus, particularly when paired with a willingness to experiment, learn, and help others adopt new tools effectively.

What we’ll expect

Your work is accurate, documented, and completed when promised. Clients feel comfortable asking you questions, and you help them understand how to use their tools. You ask for review when needed and become more independent as you gain experience.

The role offers practical experience in AI implementation, business analysis, project delivery, and training. It also provides an opportunity to develop the skills needed for an implementation lead role.

Breakaway’s AI bootcamps will help small and medium-sized business owners, presidents, CEOs, and other executives understand what AI can do for their businesses and begin applying it. The training needs to be practical enough for participants to use what they learn between sessions.

The Director of AI Learning & Bootcamps will develop the curriculum and manage the program from preparation through participant follow-up. You’ll facilitate live webinar-style sessions, support presenters, and be prepared to lead the teaching as your command of the material grows. You’ll also manage the support staff who help deliver the program.

This role connects two parts of Breakaway’s business. Bootcamps introduce leaders to practical AI use; AI Foundations helps them implement it across their companies. You’ll build a clear path between the two, working closely with marketing and the implementation team. Results from those implementations will inform future training and help attract the next group of participants.

Responsibilities

• Develop the curriculum, session plans, demonstrations, exercises, and supporting resources. Organize the material around decisions and workflows that matter to SMB leaders, with clear learning objectives for each session.
• Test demonstrations and exercises before delivery. Keep the curriculum current as tools change, and use participant questions and feedback to improve it.
• Facilitate webinar-style sessions, manage Q&A, and help presenters explain unfamiliar concepts clearly. Build the knowledge and presentation skills to conduct sessions yourself.
• Manage program schedules and the support team’s work, including participant onboarding, session production, recordings, resources, and follow-up. Establish a repeatable process that keeps delivery costs and workload manageable.
• Help participants apply what they learn. Organize support between sessions, identify where people are getting stuck, and adjust the program accordingly.
• Introduce AI Foundations at relevant points in the program and coordinate follow-up with interested participants. Document their company’s needs and readiness, arrange qualified conversations, and give the implementation team a useful handoff.
• Work with marketing on bootcamp positioning, participant communications, and enrollment. Bring client-approved implementation examples back into the curriculum and marketing so each part of the business strengthens the other.

Qualifications

• You’ve built and delivered training, workshops, cohort programs, or executive education with measurable results. You can turn a complex subject into a sequence people can follow and apply. Experience teaching business owners or senior leaders is particularly useful.
• You’ll need practical experience with AI tools and business workflows, including how to test outputs and explain their limitations. Confident facilitation, clear writing, and comfort handling live questions are essential.
• We’re looking for someone who understands both learning outcomes and the commercial side of a program. You should be comfortable discussing a paid implementation offering, recognizing a good fit, and coordinating follow-up. You’ll also need experience organizing delivery and directing support staff while contributing substantial work yourself.

What we’ll expect

Participants attend, complete useful work, and leave better equipped to apply AI. Sessions run reliably, the support team is prepared, and feedback produces specific improvements.

You’ll track attendance, completion, participant outcomes, satisfaction, and delivery costs. With marketing and the implementation team, you’ll also track qualified AI Foundations opportunities, conversion, and resulting revenue. The bootcamp must deliver on its promise while becoming a dependable source of implementation clients.

Breakaway is building practical AI bootcamps for small and medium-sized business owners, presidents, CEOs, and other executives. Our AI Foundations offering helps those businesses implement AI across their companies. Marketing needs to bring the right leaders into the bootcamps and support their progression into implementation when there’s a fit.

The Director of Marketing will be responsible for Breakaway’s content, advertising, brand, copywriting, and company voice. The primary measure of success is attracting qualified participants and turning interest into bootcamp enrollments. You’ll also build an audience and community that continue to engage with Breakaway between programs.

This is a hands-on role on a small team. You’ll create and run campaigns yourself, using AI to expand how much you can accomplish. You may direct contractors and specialist support, but writing, production, and campaign execution will remain a substantial part of your job.

Responsibilities

• Build the marketing plan around bootcamp enrollment goals and the economics of acquiring participants. Decide which audiences, messages, and channels deserve investment, and adjust based on results.
• Write and produce campaigns across social media, email, paid advertising, and the website. Build or coordinate landing pages and registration flows, and follow through from the first message to completed enrollment.
• Develop Breakaway’s brand and company voice. Write and edit clear, distinctive copy, maintain consistent presentation, and make sure claims are supported by the work we actually do.
• Turn leadership ideas, training material, participant questions, and approved client results into useful content. Establish a publishing and distribution process you can sustain with a small team.
• Grow Breakaway’s community and online presence through relevant channels, including search, partnerships, guest appearances, referrals, and direct audience engagement. Test new approaches and concentrate effort where they produce qualified interest.
• Use AI throughout research, drafting, creative development, content reuse, campaign operations, and analysis. Build reusable workflows while retaining responsibility for accuracy, quality, and voice.
• Work with the bootcamp director on launches, reminders, attendance, and follow-up. Support the path into AI Foundations, and turn successful implementations into client-approved proof for future campaigns.
• Manage the budget and any external specialists. Maintain useful tracking across lead source, registration, attendance, acquisition cost, and downstream revenue so we can understand which marketing contributes to growth.

Qualifications

• You’ve personally built and run marketing that generated customers or paid enrollments. You can explain the audience, offer, budget, and results, along with what you changed when a campaign underperformed.
• Strong copywriting and editorial judgment are essential. You should be comfortable with paid acquisition, email, content distribution, and conversion analysis, and know when specialist help is worth the cost. Experience marketing education, events, consulting, or business services to owners and executives is helpful.
• You already use AI in your work and can show how it improves your output or saves time. We’re looking for someone who enjoys making the work, learns unfamiliar tools quickly, and can take a campaign from an idea through launch and improvement with limited support.

What we’ll expect

Bootcamps attract the right participants at an acquisition cost the business can support. Breakaway’s audience and community grow, and that attention leads to registrations, attendance, and qualified implementation opportunities.

You’ll maintain a recognizable voice and a steady flow of useful work, with reporting that helps us make decisions. You should be as comfortable writing an ad or fixing a registration page as setting the marketing direction. This role suits someone who wants to accomplish a great deal with AI and a lean team.