Understand the situation. Connect the people. Put insight into action.
Ambiguity is where I do some of my best work. I learn the context, identify what matters, and help people turn an unclear situation into practical action.
A leadership transition left the annual Wild Game Dinner without critical major-donor records and supplier information. I rebuilt the operating foundation for 2025 and coordinated the volunteer teams needed to deliver the event. In 2026, I strengthened donor relationships and adapted delivery to tighter venue constraints, supporting improved donor retention and increased net surplus.
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WORKSTREAM / TASK
Event audit & gap assessment
Ownership mapping & planning timeline
Donor contact rebuild
Sponsor outreach relaunch
Venue & contract alignment
Kitchen-team alignment
Registration setup & launch
Donation procurement & vendor sourcing
Volunteer recruitment & serving plan
Menu development & event communications
Registration, ticketing & attendee follow-up
Raffle planning & fundraising logistics
Final staffing, permits & operational confirmation
Event delivery
Post-event reconciliation & financial closeout
WEEK
1
Dec 1–7
WEEK
2
Dec 8–14
WEEK
3
Dec 15–21
WEEK
4
Dec 22–28
WEEK
5
Dec 29–Jan 4
WEEK
6
Jan 5–11
WEEK
7
Jan 12–18
WEEK
8
Jan 19–25
WEEK
9
Jan 26–Feb 1
WEEK
10
Feb 2–8
WEEK
11
Feb 9–15
WEEK
12
Feb 16–22
WEEK
13
Feb 23–Mar 1
WEEK
14
Mar 2–8
WEEK
15
Mar 9–15
WEEK
16
Mar 16–22
WEEK
17
Mar 23–29
WEEK
18
Mar 30–Apr 5
WEEK
19
Apr 6–12
KEY MILESTONES
Contacts rebuilt
Week 3
Promo +
registration go
live,
Jan 1
Sponsor outreach
underway
Staffing
confirmed
Week 15
Event delivered
Week 17
Event
closeout
Week 19
WORKSTREAM
PHASES
Recovery
Planning
Outreach
Execution & Closeout
Stabilize, assess and
rebuild the foundation.
(Weeks 1–3)
Align resources, venue,
registration setup and
core event elements.
(Weeks 3–8)
Rebuild donor and sponsor
pipelines, secure donations
and mobilize volunteers.
(Weeks 3–13)
Open registration, finalize
logistics, deliver the event
and reconcile results.
(Weeks 5–19)
Takeaway:
The 2025 reconstruction enabled earlier planning for 2026. With critical resources and relationships restored, the subsequent planning cycle began in November
2025, allowing additional time for sponsor cultivation and donor development.
OPERATIONS & PROJECT MANAGEMENT / PORTFOLIO CASE STUDY
WILD GAME DINNER | OPERATIONAL REBUILD & PARTNERSHIP DEVELOPMENT
2025 — Operational reconstruction. Rebuilt major-donor contacts and supplier records to address gaps left by the
leadership transition, while restoring operating procedures and securing critical team participation.
2026 — Partnership and delivery improvements. Increased major-donor retention from 54.5% to 81.8% and expanded
raffle offerings; revenue and surplus grew despite a 26.0% increase in venue expense.
Gross Revenue: $22,014 (2025) $24,149 (2026) | +9.7%
Net Surplus: $13,460 (2025)
$14,414 (2026) | +7.1%
Annual volunteer-run fundraising dinner supporting local Scouting programs; 250 guests plus event staff in 2026.
Rebuilt event operations after a leadership transition left gaps in donor and supplier records, restoring the
relationships and procedures needed for delivery.
REBUILDING & MANAGING EVENT OPERATIONS
AT A GLANCE | PROJECT OUTCOMES
Reconstruct critical operating resources
Rebuilt major-donor contacts, supplier information, and permitting procedures that became unavailable following the
leadership transition.
Coordinated specialized operational teams
Directed cross-team planning and handoffs across kitchen, serving, bar, and front-of-house functions while coordinating
council personnel and external partners.
Maintain end-to-end project accountability
Oversaw solicitation, contracting, permitting, staffing, and operational decisions through event delivery, financial
reconciliation, and project closeout.
PROJECT TIMELINE
RECOVERY, PLANNING, EXECUTION & CLOSEOUT | 19-WEEK 2025 CYCLE
2025 event cycle: December 2024–April 2025.
Mark Kennedy
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2025 & 2026 events
1
OPERATIONS & PROJECT MANAGEMENT / PORTFOLIO CASE STUDY
PROJECT LEADERSHIP ACROSS TEAMS & EXTERNAL PARTNERS
CROSS-FUNCTIONAL EVENT STRUCTURE
Project Lead
OVERSIGHT | COORDINATION | FINAL APPROVAL
Serving Team
Meal distribution
Table coverage
Clearing & reset
Peak-demand
support
Kitchen timing
Front of House
Hall & venue setup
Guest check-in
Raffle sourcing & setup
Smaller raffle items
Donor attendance
Cleanup & breakdown
Bar Team
Alcoholic
drinks
Nonalcoholic
drinks
ID checks
Setup &
stocking
Venue & Municipal
Coordination
Venue
Contracts, dates & facility access
Municipality
Town permit coordination
Vendors, Sponsors & Donors
Sponsors | Financial & in-kind support
Donors | Game meat & product contributions
Vendors | Supplies, products & services
Raffle items | Major & smaller solicitations
Participation | Recognition & attendance
Game Dinner Event
Kitchen Team
Food ordering & inventory
Game-meat sourcing
Menu design
Food preparation
Dinner execution
Kitchen cleanup
DONOR RELATIONSHIPS &
REVENUE INITIATIVES
PARTNERSHIP MANAGEMENT & EVENT
DELIVERY
Strengthen major donor retention
Major donors ($250+ in cash or in-kind support):
retention rose from 6 of 11 (54.5%, 2024–2025) to 9 of
11 (81.8%, 2025–2026). Supported relationships
through recurring outreach, sponsor recognition, and
participation incentives.
Expand raffle revenue
Raffles were the event’s primary revenue source, and
the expanded raffle strategy—including the $2K+
Mystery Prize raffle—the largest independent revenue
source in 2026. Increased admission prices by $5 and
expanded beverage partnerships to strengthen event
offerings.
Preserve essential operating partnerships
Retained the volunteer kitchen team with dedicated
serving support and preserved independence; rebuilt
venue cooperation through reliable execution.
Coordinate dependent workstreams
Set owners and deadlines across teams; adjusted
event communications around delayed menus without
taking over kitchen responsibilities.
Adapt delivery to higher venue costs
Under a revised contract, venue expense rose from
$1,865 in 2025 to $2,350 in 2026 (+26.0%). Reduced
dining-hall reservations from six days to three and
coordinated same-night breakdown, accepting a tighter
on-site schedule without Sunday access or additional
cleaning charges.
2
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2025 & 2026 events
FUNDRAISING, PARTNERSHIPS & OPERATIONAL EXECUTION
Preparing people for organizational change takes more than announcing a new structure. This case study follows how I strengthened volunteer coverage, negotiated responsibilities, and managed resistance before and during a Scouting district consolidation. It shows the practical work behind two leadership successions, an operational district at handoff, and continued support through later staffing gaps.
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ORGANIZATIONAL CHANGE / PORTFOLIO CASE STUDY
CYC District Realignment
Mark Kennedy
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2023–2024
ORGANIZATIONAL CHALLENGE
Consolidate three districts into two amid financial,
staffing and membership pressures.
AT A GLANCE | Scouting districts coordinate support for local groups through volunteer leaders and paid staff.
MY CONTRIBUTION
Led district operations and local implementation of
the realignment, negotiated volunteer roles, managed
resistance and prepared incoming leaders.
Three existing districts realigned into two;
Quinnipiac remained separate.
Scatacook
Powahay
Aquila
11 towns
Fill color = 2023 district pre-alignment
Symbol pattern + outline = 2024 district post-alignment
2023 | FOUR-DISTRICT STRUCTURE
8 towns
Pomperaug
8 towns
5 towns
Quinnipiac
16 towns
2024 | THREE-DISTRICT STRUCTURE
Saugatuck
10 towns
Quinnipiac
16 towns
POMPERAUG SPLIT & ABSORBED
Scatacook + 3 Pomperaug towns → Aquila
Easton • Monroe • Trumbull
Powahay + 5 Pomperaug towns → Saugatuck
Bridgeport • Fairfield • Stratford
Weston • Westport
Quinnipiac: unchanged 16-town territory
Source: Council membership report (June 2, 2023).
STRENGTHENING DISTRICT OPERATIONS
VOLUNTEER ROLE REDISTRIBUTION
EXPANDING TOWN COORDINATOR COVERAGE
Coordinator coverage grew from one of five towns
to all five. Coordinators connected local groups with
schools, businesses, and community partners.
Recruited 2 coordinators directly; other leaders
recruited the rest.
-
Recruitment ended Sep 2023;
coaching/support through Mar 1.
1
2
3
Three roles held by one volunteer
One volunteer held three roles: programs,
communications and team development.
Negotiated a narrower program role
Negotiated an agreement for him to retain the
program responsibilities he valued and release
communications and team development. Coached
him through the transition.
Separate roles filled by new volunteers
Two new roles—communications and team
development—with owners found for each.
Filled January 1, 2024.
1
GEOGRAPHIC REALIGNMENT / 2023
2024
OPERATING SCOPE
831 Scouts / 29 local groups across Powahay’s five
towns (June 2, 2023).
OUTCOME
Saugatuck operational at the March 1 handoff; no
observed realignment-related interruptions.
ORGANIZATIONAL CHANGE / PORTFOLIO CASE STUDY
Managing Resistance & Leadership Transitions
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2023–2024
MANAGING SUSTAINED RESISTANCE
Months of opposition; a fixed council decision with meaningful volunteer input.
1 / CONCERNS
Loss of District identity.
Disputes over leadership
roles and influence.
A larger geographic territory.
Meaningful representation
for incoming communities.
2 / ACTIONS TAKEN
Reinforced the council’s decision to
consolidate three districts into two.
Negotiated volunteer
responsibilities.
Explored co-chair roles and
mentoring arrangements.
Facilitated volunteer input on district
identity.
3 / OBSERVED OUTCOMES
Incoming volunteers took on local
coordination and committee
leadership.
Volunteers assumed youth
advancement responsibilities.
Volunteers from separate
communities delivered events
together—workable participation,
not a claim that everyone agreed.
TWO LEADERSHIP SUCCESSIONS / BOTH APPOINTED MARCH 1, 2024
DISTRICT COMMISSIONER / Volunteer leader supporting local Scouting groups
CHALLENGE
The succession required
rebuilding trust with some
communities.
ACTIONS TAKEN
I advocated for the appointment and
helped arrange trusted alternative
contacts for those communities.
OUTCOME
Appointed March 1; independently
carrying out the role by the later
staffing transition.
MEMBERSHIP VICE-CHAIR / District-wide volunteer recruitment leader
CHALLENGE
The succession required
addressing concerns about
workload and access to support.
ACTIONS TAKEN
I advocated for his appointment, set
achievable goals, and arranged training
and experienced peer coaching.
OUTCOME
Appointed March 1; independently
carrying out the role by the later
staffing transition.
LESSONS LEARNED
Clarify roles earlier. Written descriptions existed but were inconsistent across the new organization. Duties and decision
rights needed clearer definition before the transition.
Plan staffing lead time. Descriptions were ready by fall; the revised roles were filled by January.
Complete the knowledge transfer. Appointing successors did not finish the work of transferring relationships and
operating knowledge.
2
ORGANIZATIONAL CHANGE / PORTFOLIO CASE STUDY
Executing the Transition & Sustaining Operations
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2023–2024
OVERLAPPING WORK & RESPONSIBILITIES
Preparation converged at the March 1 handoff; later Saugatuck coverage was intermittent.
2023
2024
AUG
SEP
OCT
NOV
DEC
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
Council realignment
Council staffing gaps
Council realignment: announcement to launch
Saugatuck staffing gaps
Preparation / role design
Recruitment / coaching
Recruit, coach and support volunteer town coordinators
Negotiate role redistribution and coach the program lead
Coordinate district operations and prepare the handoff
Assess leadership gaps and clarify role responsibilities
Fill open roles and coach incoming volunteer leaders
Build volunteer participation in the expanded district
Assume Quinnipiac district responsibility
Saugatuck operations and volunteer support coverage
Operations / support
Intermittent operations support
HANDOFF & CONTINUITY
March 1 — Formal handoff
Moved to Quinnipiac and transferred local contacts, event and fundraising information, and budgeting history to
Saugatuck’s incoming paid representative. Saugatuck was already operational.
Later staffing gaps — Shared coverage
Shared routine coverage and volunteer support with a District Director while retaining my Quinnipiac assignment. The
Field Director retained formal oversight.
Around August — Coverage transfer
The District Director assumed coverage. I transferred local knowledge and tapered my support.
TAKEAWAY
Saugatuck was operational at handoff, with incoming volunteers in leadership roles.
March 1, formal realignment
implementation and transition
OBSERVED PROGRAM CONTINUITY
I observed no realignment-related interruption to programs or events in the district I served.
3
AI ADOPTION · STAFF ENABLEMENT 2024–2026 · 3 PAGES
AI Adoption & Staff Enablement
I turned self-directed AI experimentation into a staff enablement initiative at Connecticut Yankee Council. I built custom GPTs for operations, research, and CFO audit preparation, with human review built into the workflows. Practical guides, individual coaching, and training for 13 staff helped colleagues use the tools independently and train others, extending the capability beyond my direct support.
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OPERATIONS & CHANGE / PORTFOLIO CASE STUDY
CYC AI Adoption & Staff Enablement
Mark Kennedy
District Executive | Operations & Change Manager
Connecticut Yankee Council | Scouting nonprofit serving youth | 2024–2026
1
AT A GLANCE | Adoption built through useful work and supported practice.
ORGANIZATIONAL CHALLENGE
Repetitive data, research and writing competed with
frontline work. Colleagues initially saw AI as a
novelty.
MY CONTRIBUTION
Self-taught, without formal AI training or mentoring;
built workflows, produced leadership analysis and
coached staff.
OPERATING SCOPE
Contact management, research, audit preparation
and in-person training for 13 staff.
OUTCOME
Faster work, executive reports, independent use by
early adopters and peer teaching.
Early results gave coworkers a reason to engage.
Cleaning and segmenting 2,000+ contact records took about 2 hours, including checks, versus an estimated 3
days. This supported Game Dinner marketing, survey distribution and volunteer outreach. Practical results built
interest; repeatable methods and coaching supported adoption.
IMPLEMENTATION THROUGH OVERLAPPING WORK
Test and develop
Apply in operations
Coach and enable
WORKSTREAM
Late ’24
Q1 ’25
Q2 ’25
Q3 ’25
Q4 ’25
Q1 ’26
Q2 ’26
After Jun
Explore and refine AI workflows
Maintain contacts / research prospects
Develop fundraising study
Build assistants and written guides
Coach staff through independent use
Prepare finance review for audit
Recurring operational use
KEY DATES & OUTCOMES
JAN 2025: Survey launch
107 responses across two districts.
SUMMER 2025: Leadership review
Findings and recommendations presented.
LATE 2025: Independent use
Four users within the early-adopter group.
2026 CYCLE: Office Manager adoption
Prepares four letters using the GPT workflow.
JUNE 3, 2026: Staff training
In-person session; three follow-up guides.
AFTER TRAINING: Peer teaching
District Director trains Development Director.
A
A
B
B
C
C
D
D
E
E
F
F
OPERATIONS & CHANGE / PORTFOLIO CASE STUDY
Custom GPTs for Research & Financial Review
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2024–2026
2
SURVEY RESEARCH: FROM RAW RESPONSES TO A LEADERSHIP REPORT
Refined questions to improve clarity and
usefulness of responses.
Across two districts, I used LLMs to refine survey questions, analyze responses and write up findings on
fundraising participation and alternatives.
107 responses analyzed; 8-page report written in 1 week
Refined GPT instructions to organize Forms
exports and identify patterns.
Decision value
Configured APA-style output: findings,
limitations and recommendations.
Presented the findings and recommendations to leadership in summer 2025.
A SPECIALIZED FINANCIAL-REVIEW GPT FOR AUDIT PREPARATION
Built a task-specific GPT to review IRS Form 990 and audit reports, then developed its output into a multi page
report for the Chief Financial Officer and Board Treasurer.
Assess requirements
Met with the CFO to clarify his goals, requirements and current approach; tailored
the tool and review process to that starting point.
Configure the GPT
Review revenue, expenses, net assets, program costs, compensation and asset
sales; separate routine changes from potential exceptions.
Structure the findings
Refined the GPT output into a review map with exact pages, sections, review
questions and follow-up priorities.
Some findings led to corrections; the CFO retained final authority.
STAGE
GPT CONFIGURATION & OUTPUT
MY REVIEW & DECISION
1 DESIGN
Designed and selected the questions; built
the branching Google Form.
2 ANALYZE
Checked raw responses line by line and
recalculated the results manually.
3 WRITE
Reviewed the report for accuracy and
incorporated feedback from two coworkers.
Turned pricing, time and parental-support barriers into recommendations for simpler
fundraisers, stronger unit margins and alternative-product pilots.
Present for review
Presented a multi page report for the CFO and Board Treasurer’s audit
preparation, identifying source pages, potential exceptions and review questions.
OPERATIONS & CHANGE / PORTFOLIO CASE STUDY
Staff Training & Capability Transfer
District Executive | Operations & Change Manager
Connecticut Yankee Council | 2024–2026
3
PROCESS STANDARDIZATION & COACHED ADOPTION
2025
BUILD & DEMONSTRATE
Built a GPT using task instructions, prior writing examples and digitized nomination
files. Prepared four recognition letters in a reported 20 minutes; the previous process
was estimated at 32 hours.
2026
GUIDE & ENABLE
The Office Manager operated the GPT at her computer. I coached the first letter, then
progressively stepped back as she completed the remaining three.
Transferred the GPT and operating method to the Office Manager, reducing dependence on one AI user.
Recognition letters were submitted for the Office Manager’s final approval, outside the 20-minute figure.
TRAIN-THE-TRAINER DEVELOPMENT
Coached the District Director in task breakdown, demonstration, written guidance and feedback, then deliberately
taught him how to train others.
The District Director subsequently trained the Development Director, extending staff support beyond the
original trainer.
IN-PERSON STAFF TRAINING & INSTRUCTIONAL DESIGN
Designed and delivered an in-person session for 13 staff on June 3, 2026, extending individual coaching into
formal staff training.
INSTRUCTIONAL FOCUS & MATERIAL
PRACTICAL CAPABILITY TAUGHT
AI literacy & prompting
Getting Started with Microsoft Copilot
Introduced Copilot, context-rich prompts, source files and
iterative follow-up questions.
Role-based analysis
Practical AI Applications for Scouting Professionals
Used fundraising, operations and leadership examples to teach
analysis, risk identification and critical questioning.
Custom GPT design
Build Your Own GPT Guide
Defined job, role, context, output and challenge rules; taught how
to test and refine the GPT.
Distributed all three guides after the session and offered individual support for getting started, building GPTs and
applying AI to each employee’s responsibilities.
Three case studies covering operations, organizational change, and AI adoption.
No side projects added yet. This space is ready for future work.
WORKING THROUGH AMBIGUITY
Clarity before momentum.
My focus: understand enough to act thoughtfully, then keep learning as the work moves forward.
01 / UNDERSTAND
Learn the situation.
Get close to the context, the people, and the constraints. Find out what’s missing.
02 / ALIGN
Make the next step clear.
Clarify priorities and responsibilities so people understand how their work connects.
03 / FOLLOW THROUGH
Act. Learn. Adjust.
Move from decisions to delivery, adapting as new information changes the picture.
BEHIND THE WORK
People first. Details matter. Clarity in ambiguity.
My background brings together behavioral science and hands-on operational leadership.
With a Master of Science in Industrial/Organizational Psychology and experience leading district operations, I’m interested in how change works in practice: what people need, how responsibilities fit together, and what keeps execution moving. This portfolio shares that work, along with projects I’m continuing to develop.
