Services
How we help
Every engagement at Enroute Advisory starts with what you want to achieve.
We begin with a complimentary 20-minute conversation to understand where you are, what you’re working toward, and challenges you’re facing. From there, we’ll determine whether Enroute Advisory is the right fit and, if so, the best way to work together.
Depending on your goals, your team, and how you like to work, there are a number of ways we can support you.
Coaching
Our coaching programs are tailored around you, your business, and what you want to achieve. There are two formats for the coaching programs:
- 1-on-1 Coaching: Work directly with our founder, Aislinn, through a coaching program designed around your goals, challenges, and business. Programs are typically structured as 90-day sprints, with clear priorities and outcomes established at the outset and progress reviewed throughout. At the end of each sprint, we assess what’s changed, what’s next, and whether another 90 days would be valuable. We’ve found that weekly sessions create the strongest momentum, but cadence can be adapted around your schedule and needs.
- Group Coaching: Led by Aislinn, group coaching brings together a small cohort of peers at a similar stage of leadership or business growth. Each session combines practical frameworks and coaching principles with real-world problem solving. Members bring current challenges to the group and benefit from facilitated coaching, diverse perspectives, and the collective experience of a trusted mastermind community.
Our coaching draws on curriculum and frameworks developed by Focal Point over decades of coaching leaders and business owners, informed by organizational research, proven methodologies, and insights from a global coaching network.
At Enroute Advisory, we complement those foundations with a modern operating lens, bringing current thinking on leadership, organizational effectiveness, technology, and AI into the conversation. Because while the fundamentals of great leadership endure, the environment leaders are operating in is changing faster than ever.
AI strategy & implementation
A 2025 MIT study found that 95% of enterprise AI pilots fail to deliver measurable financial return, a gap that often comes down to treating AI adoption as a mandate to check a box, rather than a deliberate strategy.
At Enroute Advisory, we believe the goal isn’t to use more AI, rather, it’s to build a more capable, efficient, and future-ready business. We draw on real-world experience leading AI adoption across a 150-person marketing organization at Instacart.
- We start by understanding your current state. We benchmark capabilities across individuals, teams, workflows, and the broader business to identify where AI can genuinely improve how work gets done.
- For some organizations, that means building an AI strategy from scratch. For others, it means sharpening an existing strategy, prioritizing the highest-value opportunities, or helping teams actually adopt the tools already available to them.
- From there, we can support implementation through coaching, workshops, hands-on working sessions, or an ongoing advisory partnership. The emphasis stays practical: live demonstrations, side-by-side experimentation, real workflows, and tools your team can put to work immediately.
- Opportunities to improve operational efficiency and eliminate repetitive work
- Where AI can strengthen customer experience, decision-making, and business performance
- Existing workflows and where AI can augment, automate, or simplify them
- The right mix of tools and technology based on your business needs
- Individual and team AI capability, confidence, and adoption
- Practical implementation roadmaps and priorities
- Governance, guardrails, and responsible-use practices
- The leadership behaviors and operating habits needed to turn AI into a lasting competitive advantage
Workshops & trainings
Sometimes the fastest way to create change is to get the right people in the room together.
Enroute Advisory delivers interactive workshops and training sessions virtually or in person, from focused standalone sessions to half-day and full-day experiences or multi-session programs.
Every workshop is tailored to your business, your people, and the outcome you want to achieve. Sessions combine practical frameworks, facilitated discussion, hands-on exercises, and real-world application so participants aren’t simply learning concepts. They’re applying them to the work in front of them.
The goal is for your team to leave with actionable tools, clear next steps, a shared language, and the confidence to turn what they’ve learned into lasting change.
- Leadership fundamentals
- Building high-performing teams
- Communication under pressure
- Creating accountability without micromanagement
- Navigating and leading through change
- Uncovering individual and team strengths
- Strategic planning and prioritization
- AI fundamentals for leaders and teams
- Practical AI adoption and workflow redesign
- Building an AI-ready organization
- Operational efficiency and smarter ways of working
- Custom workshops designed around a specific business challenge
Not sure where to start?
You don’t need to know whether you need coaching, training, or a combination. That’s what the first conversation is for. Tell us what’s happening in your business, where you want to go, and what’s getting in the way, we’ll help you determine the best way forward.
Frequently Asked Questions
How do we typically get started with new clients?
It starts with getting to know you, a free 20-minute conversation just to hear what you’re dealing with, followed by a complimentary deeper strategy session to go further into what’s actually going on and what a path forward could look like. From there, we prepare a proposal tailored to your situation, needs, and opportunities.
Do I need to already understand or be comfortable with AI?
Not at all. Most clients start with very little AI knowledge or skill. What matters more is a willingness to dive in. The payoff tends to come faster than people expect.
What’s the difference between 1:1 and group coaching?
1:1 is built entirely around you and your business. Group coaching puts you with a small cohort of peers at a similar stage, working through shared challenges together, once a week.
Can we work on a specific challenge without committing to ongoing coaching?
Yes, some clients come to me stuck on a specific challenge, others want a longer-term relationship, and many start with a 90-day program and end up staying longer. We tailor the engagement to what you need.
How is a workshop different from an assessment?
A workshop is a live session for a group, built around a skill or topic. An assessment is a data-backed diagnostic for a team or individual, paired with a debrief. It’s less about teaching a skill and more about surfacing exactly where things stand today.
How much does this cost?
Pricing is tailored to your program and how often we meet, so it’s best discussed on a call rather than listed here. We’ll cover it during your free 20-minute conversation or strategy session.