2026-03-17 - Jaime Haak-summary

Meeting between Dmitri Sunshine and Jaime Haak — Summary

Date: March 17, 2026 | Duration: 31 min | Via: Zoom

Overview

• RTP Technology: Startup targets 2-5% fee savings by disrupting traditional payment processes in healthcare using real-time payment tech.
• Consulting Focus: Jaime’s consulting emphasizes practical advice for founders, focusing on regulatory complexities and sustainable growth.
• Sales Strategies: Recommendations include tracking conversion rates, mapping proposal volumes, and leveraging storytelling for client engagement.
• Operational Resilience: Dmitri aims to ensure clients manage operational risks, with a focus on cybersecurity and HIPAA compliance.
• Healthcare Vision: Jaime envisions transforming healthcare to prioritize health promotion, detach insurance from employment, and enhance overall well-being.
• Networking Approach: Jaime prefers ambient networking over aggressive marketing, maintaining a small client base for in-depth engagement.

Action Items

Jaime Haak

• Forward Dmitri the fractionaljobs.io newsletter and relevant group info (e.g., fractional drops) (21:20)
• Keep Dmitri updated about her travel plans for potential meeting in May (30:04)

Dmitri Sunshine

• Review fractionaljobs.io and fractional drops newsletter forwarded by Jaime to explore fractional role opportunities (21:20)
• Coordinate with Jaime on scheduling possible hikes or meetups once she returns to the area in early May (30:07)

Key Topics

• Meeting recording announcement and casual greetings (00:00 - 02:43) — Jaime confirms current location as Santa Fe, discussing recent travel through Moab.
• Jaime shares recent personal and professional travels (02:49 - 04:32) — Attended World Health Expo in Dubai, visited Jordan, helped a friend in Boise.
• Jaime’s current professional focus (04:48 - 05:38) — Operates a health tech consulting business advising founders on monetization and startup growth.
• Jaime’s fintech startup overview (05:38 - 07:43) — Pioneering real-time payment (RTP) technology, aiming to disrupt traditional middlemen fees in healthcare payments. Currently small with a few clients, bootstrapping growth carefully.
• Jaime’s multiple engagements (07:43 - 08:08) — Executive coaching clients and various consulting assignments, emphasis on people-centric solutions over unicorn chasing.
• Discussion of Dmitri’s firm’s focus (11:02 - 12:35) — Operational resiliency with emphasis on cybersecurity, aiming to serve as a fractional CIO/CSIO ensuring smooth operations and compliance.
• Differences in healthcare cybersecurity context (12:35 - 14:11) — Stringent HIPAA and regulatory environment, challenges for startups unaware of compliance complexities.
• Challenges startups face (14:11 - 14:37) — Capital access and ability to hire operators, common chicken-and-egg scenario.
• Jaime’s stance on equities and compensation (14:37 - 15:16) — Prefers paid engagements with equity rather than free work or discounted arrangements.
• Advice to Dmitri on starting a network/consulting firm (15:16 - 18:51) — Build a sales funnel with clear conversion assumptions, focus on metrics to guide business development.
• Jaime’s unique position (19:25 - 23:31) — Deep healthcare industry experience built over decades, business leads mostly come via existing network and reputation.
• Jaime shares resources for fractional consulting roles (21:20 - 22:26) — Resources like fractionaljobs.io and fractional drops newsletter, highlighting healthcare-focused opportunities.
• Jaime’s future business ideas (24:15 - 27:58) — Complex health-related entrepreneurial concept, redefining healthcare economics by divorcing health insurance from employment.
• Dialogue about overlapping visions (28:07 - 28:47) — Dmitri mentions his Conexus community concept, focusing on localized entrepreneurial and health ecosystems.
• Planning for future engagements (29:14 - 30:44) — Jaime anticipates being in Dmitri’s area in May, potentially coordinating activities like weekday morning group hikes.

Detailed Notes

Healthcare Fintech Startup Focus

Jaime Haak is leading a fintech startup focused on real-time payment (RTP) technology to streamline payments between health insurers and providers (07:08).

• The startup aims to disrupt traditional middlemen who charge providers 2 to 5% fees for minimal services.
• RTP tech is new to the US healthcare industry, with FedNow introduced only in 2023, although it’s common globally for everyday transactions.
• The business is intentionally growing slowly and bootstrapped, leveraging Jaime’s and her co-founder’s deep healthcare product experience to manage current clients efficiently.
• Next growth step involves hiring a full-time engineer to scale once revenue volume supports expansion, drawing from Jaime’s network at Apple, Cigna, Aetna, Elevance, and Palantir.

Consulting Business and Market Approach

Jaime operates a health tech consulting business with a few clients, focusing on people-centric advice rather than bleeding-edge tech startups (06:00).

• She advises founders on making money in healthcare, emphasizing practical disruption over chasing unicorn status.
• Jaime highlighted that many startups don’t fully understand regulatory and operational complexities, creating a need for guidance on prioritizing efforts and resource use.
• Her consulting client base stays small (1-5 clients), allowing flexibility and deep engagement without formal sales funnels or cold outreach, benefiting from her long-standing industry presence.
• She engages with fractional executive communities like Fractional Jobs IO and does ambient networking rather than aggressive marketing.

Strategic Sales and Networking Advice

Jaime shared detailed strategies for building a consulting pipeline based on conversion rates and sales funnel math to Dmitri Sunshine (16:00).

• She recommends tracking warm leads with 20% conversion and cold leads with 1-3% conversion to structure outreach efforts realistically.
• Jaime advises mapping out proposal volumes needed to hit client acquisition goals, then adjusting marketing and sales activities accordingly.
• She emphasized storytelling to connect hypothetical solutions to client needs, especially when starting without an existing network.
• Dmitri was encouraged to clarify his service focus and client profile to identify relevant health tech founders Jaime advises.

Operational Resilience and Wealth Management Intersection

Dmitri described his firm’s focus on operational resilience, using cyber security assessments as an entry point to help clients (11:00).

• He aims to act as a fractional CIO/CSIO, ensuring clients avoid common operational risks like cybersecurity gaps and unauthorized access.
• Jaime noted healthcare’s unique regulatory environment complicates software operations, which aligns with Dmitri’s experience managing HIPAA-compliant child welfare software.
• Both acknowledged startups often know what they should do but lack resources or capital to execute, creating a chicken-and-egg problem around funding operational improvements.
• Jaime advised Dmitri to start small with fractional roles or executive positions to build expertise before expanding client reach.

Long-Term Vision for Healthcare Transformation

Jaime revealed a visionary idea to redesign healthcare around true health promotion, not just sick care, aiming to transform delivery, access, and economics simultaneously (25:00).

• She argues health insurance should be disconnected from employment and ideally phased out locally rather than federally.
• The concept emphasizes community-based health with access to nutrition, physical activity, social, spiritual, and financial well-being.
• Jaime highlighted the $738 billion employers spend on self-insured health plans as potential funds to redesign health systems that improve employee health and productivity.
• She plans to gradually extract people from the sick care system by offering alternative health options while maintaining necessary hospital services for acute care.

Personal and Scheduling Context

Jaime is currently traveling and working in Santa Fe with plans to return to Dmitri’s area in early May (29:50).

• Dmitri’s baby is due mid-May, which impacts his availability.
• They discussed informal plans for weekday morning hikes as a way to reconnect once Jaime returns.

Keywords

health tech consulting, fintech startup, real-time payment technology, operational resiliency, fractional consulting, healthcare innovation