90-Minute Strategy Session

Get clarity on the real issue holding you back and walk away with 2–3 concrete next steps.

Feeling stuck or second-guessing your next move?

You have refined your offer, adjusted your pricing, reworked your pitch, and tried to move things forward, but something still is not clicking.

In 90 focused minutes, we will cut through the noise, identify what is holding you back, and give you a clear path forward.

The problem:
You have made smart changes, but none of them address the real issue. The real constraint is underneath the symptoms, and you need a clear view of it before you can make your next confident move.

In a market moving quickly, this session helps you see what is actually getting in your way and helps you focus on what matters for your next phase of growth.

    What You'll Get

    During Your 90-Minute Strategy Session:

    Clarity on the real issue — We identify the specific problem keeping the business stuck (positioning, messaging, offer direction or sales friction).

    2–3 concrete next steps — You leave with an actionable plan.

    Strategic direction — Know exactly where to focus your time and energy for the biggest impact.

    Confidence to move forward — No more second-guessing, just clear direction and momentum.

    What’s Included:

    • Pre-session questionnaire so we hit the ground running
    • 90-minute strategic consultation (recorded for your reference)
    • Written follow-up summary with your 2–3 action steps
    • 7-day email support after the session for clarifying questions

    Who Its For

    This session is for creative businesses and production studios that are:

    • Spinning on the same questions without getting traction

    • Unsure what’s holding them back

    • Second-guessing their positioning, offer or next strategic move

    • Wanting an outside perspective that gets to the point quickly

    Best fit:
    You want clarity and a set of practical steps you can put into motion right away, whether you plan to implement internally or explore deeper support afterward.

    Not a fit:
    If what you need most is hands-on execution inside the session.
    This call is designed to give you direction, insight, and a clear starting point, and if implementation is the next step, I can help you choose the right path forward.

    Why This Works

    Most creative businesses don’t lack ideas. They lack a clear starting point.

    You’ve been circling the same questions for weeks—maybe months. You need someone outside your business to see what you can’t, ask the questions you haven’t asked, and cut straight to the real issue.

    In 90 minutes, we identify what’s holding you back and turn it into 2-3 clear next steps.

    If anything is unclear, I’ll refine it with you until you know how to move forward.

    Most clients describe this session as “the 90 minutes when everything finally clicked.”

    How It Works

    01 · Book Your 90-Minute Strategy Session

    Choose a time that works for you—let’s lock in your 90-minute session.

    02 · Pre-Session Prep

    I’ll send over a short questionnaire so we can dive straight into the real issues when we meet. This prep work ensures we spend your 90 minutes solving problems.

    03 · 90-Minute Strategy Session

    We’ll meet one-on-one (via video call) to:

    • Unpack what’s holding you back
    • Clarify your positioning, offer, or messaging
    • Identify the 2–3 highest-impact actions you can take immediately
    • Map your clearest path forward

    The session is recorded so you can revisit key insights later.

    04 · You Leave with Clarity & Action

    Within 48 hours, you’ll receive:

    • Written summary of your session
    • Your 2–3 prioritized action steps
    • Specific recommendations on where to focus next

    Plus, you have 7 days of email support to ask any follow-up questions as you implement.

    You walk away confident, with a clearer direction, and one specific step you can put into action immediately.

    CLIENT STORIES

    " If you’re a creative type who has the technical skills and the talent to push their career forward but doesn’t know how to navigate the landscape of connections, companies, and agents, then sitting down with Jess will provide valuable insight on what you should be doing to get yourself to where you want to be. "

    Previous to meeting Jess, I felt a little adrift in my journey as a creative, but afterward, it felt like I was handed a compass.  She helped me formalize concrete action items.  Jess listens and absorbs who you are holistically as a creative and gives guidance that feels custom to your situation.  If you’re a creative type who has the technical skills and the talent to push their career forward but doesn’t know how to navigate the landscape of connections, companies, and agents, then sitting down with Jess will provide valuable insight on what you should be doing to get yourself to where you want to be.

    JP BORCHARDT, DIRECTOR, PRODUCER, VIDEOGRAPHER & EDITOR

    " Our coaching sessions have been invaluable to me and my business. "

    I’m shooting my first TV Commercial! Jessie’s guidance gave me great actions to take and step-by-step instructions for engaging with clients. We can now connect with brands effectively and with a methodology we never had before. Our coaching sessions have been invaluable to me and my business. 

    AYO BATON, DIRECTOR, PHOTOGRAPHER & DIGITAL

    "She is definitely one of the few people I look to when I need some advice/knowledge on the industry. Can't recommend enough."

    Jessie was extremely helpful for me as an emerging photographer in the advertising industry to take the necessary steps to promote my individual brand and business further. She shared her knowledge of the industry and through her experience was able to guide me in the direction to better present my work to potential clients. She is definitely one of the few people I look to when I need some advice/knowledge on the industry. Can’t recommend enough.

    JASON GORDON, PHOTOGRAPHER

    " I highly recommend her services to any creative professional in need of guidance at any level of their career. "

    Jessie has been so incredible in giving me valuable feedback and support as I move through an important transition in my career. With her help and knowledge, I’ve been able to overcome personal barriers and learn to present and value my work as a professional. I highly recommend her services to any creative professional in need of guidance at any level of their career.

    MEAGHAN OGILVIE, PHOTOGRAPHER

    "She is a pleasure to deal with, and I'd heartily recommend her to anyone who asked."

    Jessie’s energy and experience make her an ideal advisor for an emerging commercial photographer. Whether you need help structuring your portfolio and website for maximum impact, advice on personal marketing to individual clients, or follow-up after the shoot, she can help you manage the sales aspects of your career. Jessie’s sharp eye allows her to make honest, direct suggestions that are delivered in the most constructive manner possible. She is a pleasure to deal with, and I’d heartily recommend her to anyone who asked.

    ARIC GUITÉ , PHOTOGRAPHER

    What Changes After This Session

    After 90 minutes, you’ll have:

    A clear diagnosis — You finally understand what’s been holding you back

    Confidence in your next move — No more second-guessing or spinning in circles.

    Specific action steps —  concrete next steps you can implement this week.

    Momentum — You know exactly where to focus your energy for the biggest impact.

    A path forward — Whether you move forward alone or with deeper support, you know what to do next.

     

    What’s Not Included

    This is a strategic consultation and diagnosis session

    What this session doesn’t include:

    • Hands-on execution or implementation work
    • Branding, design, or creative execution

    If you need deeper support: Often clients start with this 90-minute session to get clarity, then choose to continue with one of the implementation packages—like the Positioning Sprint, Brand Messaging & Positioning Strategy, or Business Development Accelerator.

    Investment & Payment Terms

    Investment: $650 CAD flat rate

    What’s included in your investment:

    • Pre-session questionnaire
    • 90-minute strategic consultation
    • Session recording
    • Written summary with 2–3 action steps
    • 7 days of email support

    Payment terms:

    • Payment is due at booking to secure your session
    • Accepted via credit card or e-transfer
    • Cancellation policy: Cancel or reschedule with 48+ hours notice for a full refund. Cancellations within 48 hours are non-refundable but can be rescheduled once within 30 days.

    Satisfaction guarantee: If you don’t walk away with clear next steps, I’ll work with you until you do.

    Frequently Asked Questions

    01. What happens in the 90 minutes?

    We diagnose your specific challenge, whether it’s positioning, messaging, offer direction or your next strategic move. I ask questions, we work through the issue together and you leave with 2–3 concrete next steps.

    02. Do I need to prepare anything?

    Yes, I’ll send a short questionnaire before your session so I can understand your priorities and current challenges. It takes about 10–15 minutes to complete.

    03. Is the session recorded?

    Yes. You’ll receive a recording and a written summary within 48 hours.

    04. What if I need more than 90 minutes?

    Most people get what they need in 90 minutes. If we uncover something that needs deeper support, we can continue into one of the larger packages — but there’s no obligation to continue.

    05. Can I upgrade to a larger package later?

    Yes. Many clients start here for quick clarity, then continue into deeper work. Your session fee can be applied toward a larger package if you upgrade within 30 days.

    06. Is this session virtual or in-person?

    All sessions are virtual (Google Meet). If you’re in Toronto and prefer in-person, just let me know.

    07. What if I'm not satisfied with the session?

    If you don’t walk away with clear, actionable next steps, I’ll refine them with you at no additional cost. Clarity and momentum matter.

    08. How soon can I schedule a session?

    Most sessions are available within 1–2 weeks. Once you book, you’ll receive a link to choose your preferred time.

    09. Can my business partner or team member join the session?

    Yes, you can bring one other person (co-founder, partner or key team member). If you’d like to include more than two people, let me know, and we can adjust the format.

    11. What kinds of challenges is this session best for?

    This session is ideal for quick clarity on positioning, messaging, offer direction, sales strategy or your next strategic move. If the issue is broader and needs more depth, I’ll always tell you — and point you toward the right next step.

    10. Will 90 minutes actually be enough to make progress?

    Yes. This session is designed for rapid diagnosis and clarity. You’ll leave with 2–3 targeted next steps — not vague recommendations. If deeper support makes sense afterward, we can discuss that together.

    Ready to move forward with confidence?

    Book your 90-minute session and walk away with clarity and a concrete next step.

    NOT QUITE WHAT YOU’RE LOOKING FOR?

    If you need more than strategic clarity—like full positioning work, messaging development, or sales system implementation, explore our other packages.

    Other ways we can work together:

    Positioning Sprint — 4 weeks | $6K–$12K CAD
    Working hard but unclear on your focus? Define your best-fit clients, highest-value services, and what makes you stand out.

    Brand Messaging & Positioning Strategy — 6–8 weeks | $15K–$25K CAD
    Clients not seeing your value? Build messaging that makes you the obvious choice and supports higher fees.

    Business Development Accelerator — 12 weeks | $18K–$30K CAD
    Tired of feast or famine? Install a sales system that consistently brings in the right clients.

    Growth Roadmapping & Future-Proof Blueprint — 4–6 months | $25K–$40K CAD
    Scrambling from quarter to quarter? Replace it with a clear 3–5 year plan your whole team can rally behind.

    Leadership Development & Growth Partnership Retainer — Ongoing | $5K–$15K CAD/month
    Feeling like the bottleneck? Build leaders and systems that scale with you.

    Market Expansion Research — 8–10 weeks | $12K–$20K CAD (invite-only)
    Exploring new markets? Know for sure if it’s worth it—and exactly how to enter without wasted time or money.

    Take a look at our other packages to find what your business needs.

    Leadership_development_growth_partnership

    Leadership Development & Growth Partnership Retainer

    VIEW PACKAGE

    business-development-accelerator

    Business Development Accelerator

    VIEW  PACKAGE

    Brand Messaging & Positioning Strategy

    Brand Messaging & Positioning Strategy

    VIEW  PACKAGE