Chuck Cunningham
AeroLeads people directory · profile

Chuck Cunningham Email & Phone Number

Proposal Manager at Alaka`ina Foundation Family of Companies at Alaka`ina Foundation Family of Companies
Location: Orlando, Florida, United States 10 work roles 3 schools
1 work email found @flvsglobal.net 4 phones found area 407, 571, and 813 LinkedIn matched
✓ Verified August 2026 4 data sources Profile completeness 100%

Contact Signals · 1 work email · 4 phones

Work email c****@flvsglobal.net
Direct phone (407) ***-****
LinkedIn Profile matched
3 free lookups remaining · No credit card
Role
Proposal Manager at Alaka`ina Foundation Family of Companies
Location
Orlando, Florida, United States
Company size

Who is Chuck Cunningham? Overview

A concise factual answer block for searchers comparing this professional profile.

Quick answer

Chuck Cunningham is listed as Proposal Manager at Alaka`ina Foundation Family of Companies at Alaka`ina Foundation Family of Companies, a with 476 employees, based in Orlando, Florida, United States. AeroLeads shows a work email signal at flvsglobal.net, phone signal with area code 407, 571, 813, and a matched LinkedIn profile for Chuck Cunningham.

Chuck Cunningham previously worked as Proposal Manager at Alaka`Ina Foundation Family Of Companies and FlexPoint Proposal Manager at Florida Virtual School. Chuck Cunningham holds Master Of Science (Ms), Acquisition Logistics Management from U.S. Air Force Institute Of Technology.

Company email context

Email format at Alaka`ina Foundation Family of Companies

This section adds company-level context without repeating Chuck Cunningham's masked contact details.

{first}.{last}@flvsglobal.net
86% confidence

AeroLeads found 1 current-domain work email signal for Chuck Cunningham. Compare company email patterns before reaching out.

Profile bio

About Chuck Cunningham

I use my public and private sector experience to develop compliant and compelling proposals for a wide range of professional services. As an Air Force officer, I was a Maintenance Manager, Support Commander and Acquisition Corps member. During the Iraq War, I advised the Iraqi Air Force on aircraft maintenance, and I worked side-by-side with Iraqi officers at their Headquarters in Baghdad through a period of rapid expansion of their new Air Force. After I retired from the Air Force, I worked for a nascent Small Business specializing in Information Technology Professional Services. I wore multiple hats, including business developer, capture manager, proposal manager and project manager. I joined FEMA in 2017 after Hurricane Irma and led a Public Assistance team charged with developing federal grants for Central Florida applicants who were restoring infrastructure impacted by the storm. From the start of 2020 through the Summer of 2024, I managed bid opportunities outside Florida for Florida Virtual School (FLVS), which is an online school and a contracted provider for schools and school districts throughout the U.S. During the height of the COVID-19 pandemic, I ran simultaneous, quick-turn, winning proposals for K-12 virtual learning on behalf of FLVS. As an independent consultant, I facilitated workshops on team communication using Everything DiSC®, the personal development learning experience that measures individual preferences and tendencies based on the DiSC® model. I also provided instruction on persuasion, influence and rapport. In that offering, I included influence tactics derived from my experience as an Advisor with the Iraqi Air Force. Specialties: Proposal Management, Government contracts, GSA Schedules, Governmentwide Acquisition Contracts (GWACs), Indefinite Delivery, Indefinite Quantity (IDIQ) Contracts, GovWin IQ, SAM.gov, Federal Procurement Data System, FEMA Grants Manager, Everything DiSC®

Listed skills include Dod, Military, Defense, Program Management, and 46 others.

Current workplace

Chuck Cunningham's current company

Company context helps verify the profile and gives searchers a useful next step.

Alaka`ina Foundation Family of Companies
Alaka`Ina Foundation Family Of Companies
Proposal Manager at Alaka`ina Foundation Family of Companies
Orlando, FL, US
Employees
476
AeroLeads page
10 roles

Chuck Cunningham work experience

A career timeline built from the work history available for this profile.

Proposal Manager

Current

Honolulu, Hi, Us

Certified in 2004 as a Native Hawaiian Organization (NHO), the Alaka`ina Foundation Family of Companies (FOCs) consists of Ke`aki Technologies, Laulima Government Solutions, Kūpono Government Services, Kāpili Services, Po`okela Solutions, Kīkaha Solutions, and Pololei Solutions. Our mix of capabilities, NHO procurement advantage, and contract vehicles present a strong tool set to the Federal acquisition community. These features create a total solutions package that is compelling and can support a variety of acquisition strategies. Through our total solutions, the FOCs has performed on a broad range of mission requirements. Each company represents the cohesion that we bring, as One Team with One Mission, to each and every project, program, and contract we undertake.

Sep 2024 - Present

Flexpoint Proposal Manager

Orlando, Florida, Us

Florida Virtual School (FLVS) is a fully accredited, statewide K-12 public school district. In 2000, FLVS began licensing courseware, technology, and instructional resources to schools and districts nationwide as FLVS Global. FLVS also began offering its Global School as a tuition-based online school. In 2022, FLVS unveiled FlexPoint Education Cloud® (FlexPoint®) as its national brand replacing FLVS Global. In 2023, FLVS announced that Global School is now FlexPoint Virtual School. FLVS reinvests revenue from FlexPoint into developing new digital courses and educational technologies.As the FlexPoint Proposal Manager, I produced compliant, competitive, and compelling bids for K-12 virtual learning solutions. I managed a wide range of processes which include: identifying bid opportunities; assessing bid alignment with RFP strategy; prioritizing bid resources; advising bid decisions based on scope, evaluation criteria, basis of award, and competitors; leading kick-offs and other cross-department meetings; producing proposal submissions; providing post-award reviews; analyzing bid results; and informing product strategy. To define our competitive landscape, I compiled in-depth competitor data and provides actionable information through deep-dive presentations focused on specific competitors. To enable cross-department collaboration, I created an online knowledge library with proposal and past performance content. To continuously improve our processes, I pursued automation and optimization opportunities.I joined FLVS as their Global Proposal Coordinator at the start of 2020. FLVS promoted me to Proposal Manager after I led bids worth >$6-million in revenue in my first full fiscal year with the school. For the 2020-21 school year, I surged bid production to rapidly respond to the pandemic-driven demand for K-12 online curriculum. Contract awards from those bids exceeded $5.5-million, including the first-ever Federal contract for FLVS.

Aug 2021 - Sep 2024

Trainer/Facilitator

Rolling Meadows, Il, Us

TrainSmart is a full service learning solutions and talent development provider serving clients around the world. TrainSmart provides a wide range of training and development solutions. In addition to successful workshops, TrainSmart provides assessments and analysis, consulting, coaching, project management, and continuous improvement programs.As an Independent Consultant, I facilitated team communication workshops, based on Everything DiSC®, which prepares people to be more capable and productive by: 1) helping them better understand their behavior styles and the styles of their coworkers; 2) developing behavior-based communication skills as the foundation for building other key competencies; 3) defining the phases of team development and identifying how leaders can guide teams through all development phases; and 4) building trust and commitment among team members. I also provided instruction on persuasion, influence and rapport including situation-specific influence tactics.

Apr 2014 - Jan 2020

Emergency Management Specialist (Recovery)

Washington, Dc, Us

FEMA's primary purpose is to coordinate disaster responses that have overwhelmed the resources of local and state authorities. FEMA programs include Public Assistance (PA) grants for debris removal, emergency protective measures, and public infrastructure restoration. PA is FEMA’s largest grant program.I joined FEMA after Hurricane Irma to develop PA grants for Florida applicants. The storm was a Type I Major Disaster which impacted every county in the state. I was a Task Force Leader for a team of Program Delivery Managers (PDMGs) assisting (46) applicants throughout Central Florida, from Palatka to Port St. Lucie. I coached and mentored the PDMGs, set performance objectives for them, tracked their projects, and resolved policy issues for the applicants. I also coordinated our projects with FEMA specialists in Environmental and Historic Preservation, Hazard Mitigation Assistance, and Insurance.I implemented FEMA’s new PA delivery model for the applicants and mastered the web-based Grants Manager tool for capturing damages, formulating projects, and transitioning grants to funds obligation. Using Grants Manager, I validated damage inventories totaling $100-million for (3) Counties, (25) municipalities, (4) utilities, (3) colleges, (6) Private Nonprofits, a Housing Authority, and a hospital. I supervised formulation of over (450) projects — (250) projects worth $27.8-million were obligated within (18) months of the storm and (70) additional projects advanced to Final Reviews by the State and applicants representing another $71.9-million. I also guided review and approval of (137) site inspections and Damage Description and Dimensions (DDD) documents.Leveraging 20+ years of Government contracts experience, I assessed applicant compliance with Federal requirements for Procurement Under Grants, including Title 2 of the Code of Federal Regulations, and Federal Acquisition Regulations. When required, I proposed remedies for applicant compliance issues.

Dec 2017 - Aug 2019

Business Development Manager

Tampa, Florida, Us

PTP is a service-disabled veteran owned small business (SDVOSB). PTP’s core competencies evolved from leveraging IT enablers for knowledge management, such as SharePoint, with an emphasis on web-based Knowledge Portals and Portal Services. PTP’s capabilities expanded significantly after I left.After retiring from the Air Force, I joined PTP and performed a variety of functions. I created processes and tools from scratch for analyzing bid opportunities and informing engagement and capture strategies. I formed and led cross-functional proposal teams, which included teaming partners and consultants. I authored management plans and technical solutions for multiple responses to Government solicitations for professional services contracts. I led PTP’s successful bid for knowledge management services for the Army XVIII Airborne Corps, which was the firm’s first prime contract. I led PTP’s successful bid for a Navy SeaPort-e prime contract, which was the firm’s first multiple award contract. I also leveraged the SeaPort-e award to trigger the first government audit of the firm's accounting system; PTP’s successful DCAA audit confirmed their qualification for award of cost-reimbursement contracts. Post award, I implemented professional services contracts and task orders for Joint and Army customers. I was also the task manager for a software development team which devised a solution for automating the initial, data-heavy phases of the Military Decision Making Process.To expand PTP’s corporate capabilities and certifications, I pursued a Mentor-Protégé opportunity through the DoD Program. I co-authored PTP's Mentor-Protégé agreement for the Missile Defense Agency which was approved in record time. Upon completion of the program, PTP received the prestigious Nunn-Perry Award as recognition of their development and growth.

Oct 2012 - Aug 2017

U.S. Air Force Officer (Retired)

Randolph Afb, Tx, Us

I was a Maintenance Officer, Support Commander, and Acquisition Corps member. Over the course of my career, I led aircraft and munitions maintenance units at the organizational, intermediate and depot levels and performed nuclear weapons duties in support of extended deterrence for the North Atlantic Treaty Organization. Along the way, I took advantage of a career-broadening opportunity to gain unique experience as a program manager in the National Imagery and Mapping Agency (now NGA). I subsequently applied that experience to multiple contract management roles, including Government Task Lead (GTL), Contracting Officer’s Technical Representative (COTR) and Functional Commander for Performance-Based Contracts. I excelled in international environments while advising and working side-by-side with the Hellenic Air Force (HAF), the Italian Air Force (ItAF) and the Iraqi Air Force (IqAF). I served four times in Europe, including three squadron commander assignments. I deployed to the Balkans as the Director of Logistics and Support for an Air Expeditionary Wing. I also deployed to Baghdad as an Aircraft Maintenance Advisor. There, I helped Iraqi Air Staff senior officers deal with the rapid growth in their new Air Force. Late in my career, I supervised joint operational testing for Command and Control & Combat Support (C2&CS) systems at the Air Force Operational Test & Evaluation Center. I completed my Air Force career working for the Assistant Chief of Staff, Strategic Deterrence and Nuclear Integration (AF/A10) at the Pentagon, where I led assessments of Nuclear Enterprise health for senior leaders.

May 1987 - Aug 2012

Deputy Chief, Nuclear Enterprise Assessments Division

Randolph Afb, Tx, Us

I completed my military career as a staff officer at the Pentagon where I set up a new Air Force Headquarters branch, tasked with analyzing the health of the Nuclear Enterprise and producing assessments for the Secretary of the Air Force and the Air Force Chief of Staff. I leveraged government auditors (Air Force Audit Agency) and a global policy think tank (RAND Corporation) to independently assess nuclear weapons management initiatives. I orchestrated early involvement by the Assessments Division (AF/A10-A) in the 2012 update of the Air Force Strategic Plan. I oversaw development of a decision support tool enabling decision-quality analysis of progress towards achieving Air Force Strategic Plan goals and objectives and overall Nuclear Enterprise health. I assisted with coordinating the inaugural Air Force nuclear war game specifically designed to produce courses-of-action for strategic planners — this was the first in a series of war games which answered the Air Force Chief of Staff vector to revitalize deterrence thinking. As a sustainment subject matter expert, I validated results from the Chief of Staff-directed annual assessments of nuclear sustainment. Additionally, I codified the Headquarters processes for capturing the findings from these assessments and tracking the development and implementation of counter-measures at the Enterprise level.

Jun 2009 - Jul 2012

Aircraft Maintenance Advisor

Us

I worked side-by-side with the Iraqi Air Staff in Baghdad on acquisition and sustainment of aircraft and support equipment for their new Air Force and served as Chief-of-Staff for a 21-member USAF and RAF advisor team for the Iraqi Air Staff. I mentored Iraqi officers through rapid growth in their new Air Force — maintenance capacity increased by 50% over seven months and weekly sorties surged 1000%. I managed sustainment of Iraqi rotary-wing aircraft as Government Task Lead (GTL) for U.S.-funded Contractor Logistics Support (CLS). In that role, I set up and managed supply chains for U.S. and Russian manufactured parts and assemblies. I also advised the Iraqi Air Staff on execution of their CLS contract as part of their C-130 foreign military sales package from the U.S., and I assisted them with developing CLS requirements for the rest of their fixed-wing aircraft. The capstone of my time in Iraq was my collaboration with Iraqi Air Staff officers to codify their acquisition, maintenance, and training plans in a single, integrated Sustainment Roadmap, which became the cornerstone of their long-range plans.

Jul 2007 - Jul 2008
Team & coworkers

Colleagues at Alaka`ina Foundation Family of Companies

Other employees you can reach at alakainafoundation.com. View company contacts for 476 employees →

3 education records

Chuck Cunningham education

Master Of Science (Ms), Acquisition Logistics Management

U.S. Air Force Institute Of Technology

Bachelor Of Science (Bs), Business Management

United States Air Force Academy

Education record

U.S. Air Force Academy Preparatory School
FAQ

Frequently asked questions about Chuck Cunningham

Quick answers generated from the profile data available on this page.

What company does Chuck Cunningham work for?

Chuck Cunningham works for Alaka`ina Foundation Family of Companies.

What is Chuck Cunningham's role at Alaka`ina Foundation Family of Companies?

Chuck Cunningham is listed as Proposal Manager at Alaka`ina Foundation Family of Companies at Alaka`ina Foundation Family of Companies.

What is Chuck Cunningham's email address?

AeroLeads has found 1 work email signal at @flvsglobal.net for Chuck Cunningham at Alaka`ina Foundation Family of Companies.

What is Chuck Cunningham's phone number?

AeroLeads has found 4 phone signal(s) with area code 407, 571, 813 for Chuck Cunningham at Alaka`ina Foundation Family of Companies.

Where is Chuck Cunningham based?

Chuck Cunningham is based in Orlando, Florida, United States while working with Alaka`ina Foundation Family of Companies.

What companies has Chuck Cunningham worked for?

Chuck Cunningham has worked for Alaka`Ina Foundation Family Of Companies, Florida Virtual School, Trainsmart, Inc. - Learning & Development Solutions - Soft Skills Training - Elearning Development, Fema, and People, Technology And Processes Llc.

Who are Chuck Cunningham's colleagues at Alaka`ina Foundation Family of Companies?

Chuck Cunningham's colleagues at Alaka`ina Foundation Family of Companies include Solomon Raphael, Msm, Mba, Britney Cross, Diana D'Agostino, Fredric Lewis, and Andrew Taylor.

How can I contact Chuck Cunningham?

You can use AeroLeads to view verified contact signals for Chuck Cunningham at Alaka`ina Foundation Family of Companies, including work email, phone, and LinkedIn data when available.

What schools did Chuck Cunningham attend?

Chuck Cunningham holds Master Of Science (Ms), Acquisition Logistics Management from U.S. Air Force Institute Of Technology.

What skills is Chuck Cunningham known for?

Chuck Cunningham is listed with skills including Dod, Military, Defense, Program Management, Air Force, Security Clearance, Command, and Leadership.

Find 750M verified contacts

Search by job title, company, industry, location, and seniority. Export verified B2B contact data when you need it.