— How we work —

A coordinated practice for a complicated life.

When wealth gets complicated, the usual answer is to add more specialists — more accountants, more lawyers, more advisors, each looking at their own slice. The problem is that the slices stop adding up to a picture. Cherry Hill is built differently. We're the team that holds the whole picture, works alongside your specialists, and gives the household one consistent view of what's happening, what's coming, and what to do about it.

— The model —

One team. One plan. One coordinated experience.

Our experts handle the planning, investments, insurance, and estate work in-house. When there's an outside advisor — your accountant, your lawyer, your banker — we make sure they're working from the same context we are. When a life event hits, the right people already know. Your specialists do what they do best. We hold the whole picture.

Insurance products are sold via Harbourfront Estate Planning Services Inc. (HEPSI). These products are not subject to CIRO regulation or CIPF coverage. Please inquire for more information.

How coordination works at Cherry Hill Cherry Hill sits at the centre, connected by lines to seven nodes — you and your six specialists (accountant, lawyer, banker, insurance, investments, estate) — forming one coordinated picture in which every professional works from the same context. You You — your household, at peace, in the loop Accountant Your accountant — tax position kept in sync with the plan Lawyer Your lawyer — estate documents aligned with the whole picture Investments Investment strategy informed by tax, estate, and cash needs Estate Estate planning that aligns with the full financial picture Insurance Insurance coverage reviewed against the entire picture Banker Your banker — lending and liquidity coordinated with the plan

Single point of contact.

You call one number. Whatever you need — tax, legal, insurance, investments — we figure out who needs to be involved and what needs to happen, and we drive it.

Decisions made in context.

No siloed advice. Every recommendation accounts for the rest of the picture. The tax decision considers the estate plan. The insurance review considers the business structure. The investment shift considers cash needs three years out.

Proactive, not reactive.

We track what's coming — return season, year-end, life-stage transitions — and surface the work before it surfaces itself. Most clients say the same thing: "I forget about this stuff because they don't."

Okanagan vineyard rows leading toward the lake and distant mountains

— The Pathway —

A structured path through complexity.

Working with us follows a documented five-phase pathway. It's not a sales process — it's how we actually get a complicated financial life organized, and then how we keep it organized. Each phase has clear deliverables and a clear handoff to the next. When the Pathway ends, the rhythm of the relationship begins.

Phase i

Investment Onboarding

Most clients arrive with investments scattered across accounts, accumulated over years — some still serving them, some that aren't. We bring everything over, look at tax implications before any move, and put the right investments in the right accounts. We change what isn't working, keep what is, and add the public and private market strategies that round out the picture. Every holding has a purpose. If it doesn't, it shouldn't be in your portfolio.

More on how we invest

Phase ii

Financial Planning

Your goals drive the plan; the plan drives every decision that follows. We work through what matters to you — the lifestyle you're building, the people you're providing for, the legacy you want to leave, the things you'd never compromise on — and translate it into a financial roadmap. Cash flow, retirement income, tax positioning, what's funded and what isn't. The plan is a living document. It evolves as your life does.

More on how we plan

Phase iii

Insurance

People accumulate policies the same way they accumulate advisors — a bit at a time, often without revisiting whether what they bought ten years ago still fits the life they're living today. Our job is to look honestly: what coverage genuinely matters now, what gaps actually exist, and what policies are charging premiums without serving a purpose anymore. Sometimes we add coverage. Sometimes we right-size it.

More on our approach to insurance

Phase iv

Estate & Legacy

What you've built deserves to go where you intend it to go, with the people you trust to carry it, and without the family confusion that estate work too often leaves behind. We work alongside your lawyer and accountant to make sure your will, your powers of attorney, your beneficiary designations, and your corporate structure all point in the same direction. Then we make sure the people who'll actually run the estate — your executor, your family — understand what you've decided and why.

More on estate and legacy work

Phase v

Annual Family Office Review

By Phase 5, the onboarding work is done. Your investments are placed, the plan is live, the insurance fits, the estate is in order. From here, the rhythm shifts. The Annual Family Office Review is the formal anchor — once a year, we walk through a Total Wealth Summary together: how the investments performed against the baseline, what's changed in your life and plan, what needs attention, what's coming. Between annual reviews, we run semiannual portfolio reviews, refresh planning assumptions as your life evolves, and host clients at Family Office education and private-market sessions. The Pathway is finite. The work isn't.

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— Take the next step —

Let's coordinate.

We work with a small number of households at a time. If what you've read here feels like the kind of relationship you've been looking for, the next move is a conversation. No agenda, no pitch — just a chance to see if there's a fit.

Start a conversation