Meeting between Dmitri Sunshine and Caryn Paer — Summary
Date: March 20, 2026 | Duration: 43 min | Via: Zoom
Overview
- Caryn Paer and Dmitri Sunshine discussed the evolving role of a fractional operating leader, emphasizing the importance of carving out a niche in the competitive market.
- They are currently in early stages, working on client acquisition without any paying clients yet.
- Caryn targets high-growth tech firms in financial services, while Dmitri focuses on RIAs (Registered Investment Advisors) under $1.5 billion in assets.
- They discussed the value of community through fractional leadership guilds and are utilizing tools like CRM for business operations.
- Both participants acknowledged the significance of networking and relationship-building, as well as the importance of mental health and personal motivations influencing their business journeys.
Action Items
Caryn Paer
- Send Dmitri her fractional operating leader one-pager PDF (31:38)
- Continue refining and publishing LinkedIn content to build thought leadership (33:30)
- Share nonprofit mental health campaign posts for Dmitri to help promote (40:07)
- Finalize branding materials and website content with the hired designer (40:36)
- Stay connected and follow up after the meeting (41:52)
Dmitri Sunshine
- Share Human Agency and fractional-related platform links with Caryn (09:12)
- Send Caryn his service one-pager for mutual client referrals (31:38)
- Host a fractional ‘show and tell’ salon and invite Caryn to participate when ready (36:20)
- Help promote Caryn’s mental health nonprofit posts on LinkedIn (40:10)
Key Topics
- Caryn clarified her role as a ‘fractional operating leader’ rather than COO due to varying interpretations
- Both participants are new to their current ventures and have yet to secure clients
- Caryn focused on refining her offers, niche, and ICP through LinkedIn publishing and networking, especially in NYC
- Discussed networking groups relevant to health, financial services, and global companies
- Caryn uses a CRM system integrated with ‘Go High Level’ for scheduling and payment processing (~$100/month)
- Dmitri targets RIAs with less than $1.5 billion AUM due to new regulations
- Emphasized persistence in relationship-building with anecdotes about follow-ups
- Plans for Dmitri to host a ‘show and tell’ salon for fractional professionals
- Mental health was a mutual interest with plans to support Caryn’s nonprofit campaign launching in May
- Dmitri announced the expected arrival of his baby boy on May 15th
Detailed Notes
Fractional Operating Leadership Strategy
- Caryn Paer avoids the term COO due to its broad meanings and prefers “fractional operating leader”
- She is actively shaping her niche and offers based on ongoing market validation and networking feedback
- Neither Caryn nor Dmitri currently have paying clients, reflecting early venture stages
- Caryn prioritizes high-growth tech companies selling financial services as her top segment
- Private equity-backed RIA aggregators and insurance roll-ups are secondary and tertiary focuses
- Dmitri targets RIAs under $1.5 billion in AUM, especially due to upcoming new regulations effective in June
Marketing and Outreach Tactics
- Caryn initially posted consistently on LinkedIn for about 4-5 weeks but paused due to increased networking events
- Reposting older content after a quarter is recommended to maintain presence
- Dmitri emphasizes targeting individuals currently experiencing pain points for better engagement
- Caryn uses LinkedIn Premium but has not yet invested in Sales Navigator
- Caryn’s CRM is built on Go High Level, costing around $100/month including setup help
- Dmitri shares advanced automation using Claude Code with API keys, spending about $200/month on top-tier access
Business Development Insights
- Caryn recounts a discouraging call with a private equity board member dismissing the need for her services, who then reached back out with a new acquisition needing operational help
- Dmitri explains the difficulty of entering wealth management due to slow processes and strong trust requirements
- Both agree targeting private equity-backed companies demands patient, relationship-driven approaches
Community and Collaboration
- Dmitri plans to host a “show and tell” salon for four fractional professionals to share key learnings
- Both share passion for mental health; Caryn sits on a nonprofit board focused on underserved children’s mental health
- Caryn plans to launch a mental health awareness campaign in May, aligned with Mental Health Awareness Month
- Dmitri offers to help share content through his network
Personal Context
- Dmitri shares upcoming arrival of a baby boy due May 15th, his first with his wife but third child overall
- Previous mental health challenges were linked to sleep deprivation
- Caryn’s sons are ages 19 and 21; she left a full-time role at Citibank in September to pursue fractional leadership
Keywords
Fractional Operating Leader, Networking Strategies, LinkedIn Outreach, Private Equity Backed Companies, Mental Health Advocacy, Cybersecurity Insurance