Principle 1
Hyperscale your people, not replace them.
AI amplifies adviser judgment and client service quality. It does not automate the relationship.
Obermeyer Wealth Partners · July 2026 · Confidential
AI Adoption Roadmap.
A strategic proposal
for Obermeyer Wealth Partners.
AI is the tool. Your people are the advantage. A four-phase plan grounded in your own governance, your own team, and use cases they named on July 1.
- $2.9B
- AUM
- 660
- Client accounts
- 31
- People
- 3
- Offices
Section 01 · Executive Summary
You have already done the hard governance work. Now you implement.
Obermeyer is one of the most respected independent wealth firms in the Rocky Mountain region. A multi-family office that grew, selectively, into a top-ranked RIA. $2.9B AUM, 660 accounts, 31 people, offices in Denver, Aspen, and Vail. A tight, high-trust team at an extraordinary ratio of assets to headcount.
That efficiency is your competitive edge, and it is the reason AI matters right now. Your growth plans are ambitious, but you are not scaling by adding headcount. You are scaling by making every adviser, client service professional, and operations person measurably more capable.
What separates Obermeyer from most firms is that the AUP is drafted, the Governance Committee Charter is in place, and the working group is moving deliberately. Most firms are still debating whether to start. You are ready to implement.
Principle 2
Crawl, walk, run.
Fluency first. High-value quick wins second. Enterprise-scale automation third. No one gets left behind.
Principle 3
Parallel streams.
AI adoption runs alongside your ongoing systems and compliance work, not in competition with it.
Obermeyer has every ingredient for a successful AI transformation: committed leadership, a governance foundation already in place, a team that has started using the tools, and clear, specific use cases with measurable business value. This roadmap turns that raw material into a coordinated, firm-wide capability.
Section 02 · Readiness Assessment
Meaningfully ahead of the baseline.
Most financial services firms of your size and structure score in the 4.5 to 5.5 range. What brings Obermeyer's score to 6.5 rather than higher is the gap between policy and firm-wide practice, and that gap is exactly what this roadmap closes.
0.0out of 10
UpShift AI Readiness Score
Strengths
- Governance architecture is ahead of most peer firms — AUP and Committee Charter are drafted and in active revision.
- Executive sponsorship is real. Susan, Adam, Dana, and Steve are not just supportive — they are already using the tools.
- Adam's investment team is running sophisticated Claude Teams workflows for SEC filing analysis, standardized research, and screening.
- Dana's advisory team has normalized daily AI use for email drafting, meeting prep, and client follow-up.
- Steve brings compliance AI experience from a prior organization and has piloted Copilot for marketing rule review.
- The firm runs lean — 31 people, $2.9B AUM — which means AI ROI hits faster and harder than at a bloated organization.
Gaps and Risks
- The AUP and Committee Charter have not yet been rolled out to the full firm. Policy exists on paper but not in practice.
- Client service is the highest-volume, highest-friction part of the business and has the lowest current AI adoption.
- Orion and Salesforce are not connected. Manual synthesis between portfolio data and client data is a persistent drag.
- No active Microsoft 365 connectors. SharePoint and Teams data is not queryable through Copilot or Claude.
- Feathery is four months into a six-week rollout. A vendor dependency risk that needs a contingency plan.
- Cohort-based training has not started. Individual adoption is uneven and not institutionalized.
Section 03 · Discovery Findings
Ten findings from your team, on July 1.
These are not interpretations. They are what Susan, Allie, Adam, Dana, and Steve told us, consistently and with specificity.
Section 04 · Prioritized Opportunities
Fourteen opportunities, ranked by business impact.
These are the workflows we've identified with the firm, listed in order of priority. They are the outcomes the training program is designed to produce.
High priority
AUP Firmwide Rollout
Policy is written. Deploy it to all 31 employees with acknowledgment tracking and a Q&A resource. The governance foundation everything else depends on.
High priority
Client Email Drafting System
Dana alone spends 2–3 hrs/day on client email. A standardized prompt library and review workflow for advisory and client service email delivers immediate, measurable time recovery.
High priority
Client Meeting Package Automation
Automate the six-report Orion package assembly. Eliminates 90-plus manual report runs per day across the firm.
High priority
RM Investment Intelligence Access
Queryable interface giving RMs real-time access to Adam's investment research, weekly notes, and portfolio themes. Highest strategic leverage item in the firm.
High priority
Estate Distribution Calculator
AI-assisted share division and rounding logic for estate accounts. Eliminates a recurring client service pain point that carries compliance risk when done manually.
High priority
Compliance Calendar Automation
AI-managed compliance calendar with regulatory deadlines, sequential filing steps, and monitoring alerts. Steve's top stated priority.
High priority
SharePoint Knowledge Layer
Activate Copilot connectors to make SharePoint policies, procedures, and firm knowledge queryable in plain language.
High priority
Marketing Disclosure Workflow
Build on Steve's Copilot pilot: structured workflow for marketing material compliance review and disclosure drafting against the marketing rule.
Medium priority
Word to PowerPoint Pipeline
Automated conversion of Word outlines and compliance memos to formatted PowerPoint. Also valuable for advisory presentations.
Medium priority
Salesforce + Orion Intelligence Bridge
AI layer querying both systems for meeting prep and personalized reporting. Highest infrastructure value in the firm when complete.
Medium priority
Daily Adviser Brief
Personalized morning brief: five priority actions, upcoming client meeting prep, relevant portfolio flags, and scheduling gaps.
Medium priority
Agentic Research Pipeline
Fully automated investment research: scheduled ingestion from SEC filings, AlphaSense, and Bloomberg, synthesized into standardized reports.
Medium priority
Client Onboarding Paperwork
AI-assisted form completion for account opening. Assess Feathery status and build contingency if the vendor rollout does not close.
Low priority
Client Onboarding One-Pager
Scale the one-page client summary pilot Dana's team has tested to all new onboardings. Automated generation from Salesforce with adviser review.
Section 06 · Training Investment
Two ways to run the training.
The training scope is broken into two modular investments, so you can right-size to the audience you want to activate first. Third-party costs (Anthropic licensing fees) are billed directly to Obermeyer by the provider and are separate.
Option A
Live Workshop Program
4 live sessions · 3 office hours · 4 or 8 weeks
$61,250
$1,750 per person · 35 staff
The build-your-own-workflow program. Live training with role-based exercises, a custom wealth management prompt library, and dedicated leadership coaching.
- 4 live training sessions (90 min)
- 3 office hours blocks (45 min)
- All three tracks: foundational, applied, leadership
- Role-based small-group workshops
- Dedicated leadership & governance session
- Custom wealth management prompt library
- 4-week intensive or 8-week embedded — your pace
Everything Susan outlined. Our recommendation for Obermeyer Wealth Partners.
Option B · Recommended
Full Fluency Program
6 live sessions · 5 office hours · deep application labs
$87,500
$2,500 per person · 35 staff
AI delivered deeper and embedded into real workflows. More sessions, deeper labs, and built-in compliance and governance support.
- 6 live training sessions (90 min)
- 5 office hours blocks (45 min)
- All three tracks + deep application labs
- Champion enablement session
- Custom prompt library + workflow templates
- Compliance module + governance policy support
Recommended. Ongoing champion support and the Section AI platform are separate optional add-ons.
Payment terms. 50% upon engagement start, 50% at program completion. Training options can be invoiced independently of the governance and tooling workstreams. Third-party licensing fees are billed directly by the provider.
Section 07 · About UpShift
AI is the tool. Your people are the advantage.
UpShift Collective is a Vancouver-based AI consulting and training firm. We work with executives, leadership teams, and knowledge workers to help them adopt AI with confidence, clarity, and measurable business impact. We are not a vendor selling software. We are practitioners who have deployed AI inside real organizations, and we build your internal capability so you do not need us forever.
We start with a deep understanding of your business, your people, and your constraints. We build what you actually need, not a generic curriculum. We train alongside you, measure outcomes, and adjust. You own everything we build together.
- Thousands of executives trained across financial services, professional services, real estate, healthcare, and technology.
- Exclusive YPO distribution rights for the Lean Startup Method.
- Certified AI Consultant, WSI Technology International; Super Trainer, VJAL Institute.
- Prior exits: Walker Group (acquired by Industrial Alliance); Bounce (early ML platform deployed with AT&T).
Section 08 · Next Step
You have built the governance foundation before the adoption pressure hit. Now we deploy it.
Obermeyer is positioned to lead in a way that protects your clients, respects your compliance obligations, and makes your people better at what they already do well.