Executive Director Application Step 1 of 9 11% Before You Begin Please have the following documents ready to upload at the time of form completion. (PDF format accepted)– Your resume– Your cover letterYour application is considered incomplete until your resume and cover letter are received and this form is completed.Application review will begin on March 16, 2026.We encourage you to thoroughly review all posted materials – including the application instructions, foundation profile, and benefits information – before submitting an application.Please, no telephone calls. General questions may be directed to hiring@milltowncharitablefoundation.org.This field is hidden when viewing the formUntitled Your Personal InformationName(Required) First Last Email(Required) Phone(Required)Location(Required) City State / Province / Region Application QuestionsPlease complete the questions below to accompany your application materials. Preferred PronounsWe invite you to share your preferred pronouns (e.g. she/her, he/him, they/them). This is entirely optional and offered to support inclusive and respectful interactions.Are you currently authorized to work in the United States without need for current or future visa sponsorship?(Required) No, I am not authorized to work in the U.S. I am authorized now but will need sponsorship in the future. Yes, I am authorized without the need for sponsorship. Are you willing to undergo a background check in accordance with federal, state, and local law/regulations?(Required) Yes No This role includes a mix of remote work and on-site visits in Berkshire County, MA. Please select the option that best describes your situation.(Required) I currently live within commuting distance of Berkshire County. I do not currently live within commuting distance, but am willing to relocate if offered the position. I do not currently live within commuting distance and do not have a relocation plan. Do you have a valid driver's license and reliable transportation to travel throughout Berkshire County and other areas of Massachusetts, year-round, to attend meetings and events?(Required) Yes, I have a valid driver’s license and reliable transportation. No, I do not have a valid driver’s license or access to reliable transportation. I do not have a valid driver’s license, but have access to reliable transportation. Please describe your compensation expectations.(Required) Self-Assessment Please complete this self-assessment thoughtfully. This tool is designed to help you reflect on your qualifications and provide our hiring team with additional context about your experience and fit for this role. There are no “right” or “wrong” answers—we value authenticity and self-awareness.This field is hidden when viewing the formUntitled Section 1: Experience & QualificationsLeadership Experience(Required)How many years of senior leadership experience do you have in philanthropy, non-profit management, or education-focused organizations? Less than 5 years 5-7 years 7-10 years 10-15 years More than 15 years Please briefly describe your most relevant senior leadership role(s):(Required)Formative Stage Experience(Required)Have you worked in an organization during its formative or startup stages? Yes, I founded an organization. Yes, I joined within the first 1-2 years. Yes, I led a major expansion or transformation. Some experience with startup environments. No, but I am eager to learn. Formative Stage Experience: If YesIf yes, please describe your role and the stage of the organization:Fundraising Experience(Required)Please rate your experience level in the following fundraising areas:No ExperienceSome ExperienceModerate ExperienceSignificant ExperienceExpert LevelIndividual Donor CultivationFoundation GrantsCorporate GivingMajor Gift CampaignsDonor StewardshipWhat is the largest fundraising goal you have successfully led? Please provide approximate dollar amount and context.(Required)Educational Programming(Required)Rate your knowledge / experience in educational program development: Deep expertise – I have designed and implemented multiple educational programs Strong knowledge – I have overseen educational initiatives Moderate knowledge – I have worked adjacent to educational programming Basic understanding – I have awareness but limited direct experience Limited knowledge – This would be a growth area for me Please describe your most relevant experience with educational programs or grantmaking:(Required) Section 2: Core CompetenciesStrategic Management(Required)How would you describe your approach to strategic planning and execution?Can you provide a brief example of a strategic initiative you led from vision to implementation?(Required)Financial & Operational Management(Required)Rate your comfort level with the following:Not ComfortableSomewhat ComfortableComfortableVery ComfortableBudget Development & ManagementFinancial Reporting & AnalysisOperational Systems DesignCompliance & Regulatory RequirementsTeam Management & HRCommunication & Relationship Building(Required)Rate your comfort level with public speaking and serving as the face of an organization: Very comfortable – I actively seek these opportunities Comfortable – I do this regularly and effectively Somewhat comfortable – I can do this when needed Still developing – I would benefit from coaching Describe your experience building partnerships with diverse stakeholders (schools, nonprofits, community leaders, donors, etc.)(Required) Section 3: Working Style & Cultural FitEntrepreneurial Mindset(Required)How comfortable are you working in ambiguous situations with minimal direction? Highly comfortable – I thrive in ambiguity and startup environments Comfortable – I can navigate uncertainty effectively Somewhat comfortable – I prefer some structure but can adapt Less comfortable – I work best with clear direction Describe a situation where you had to build something from the ground up with limited resources or guidance:(Required)Data-Driven Decision Making(Required)How do you balance intuition with data in your decision-making?Provide an example of how you have used metrics or data to improve program outcomes:(Required)Strategic vs. Hands-On Balance(Required)How would you describe your leadership style? Primarily strategic – I focus on vision and delegation Balanced – I move between strategic and operational as needed Primarily hands-on – I like to be involved in execution Context-dependent – I adapt based on the situation As the founding Executive Director, this role requires both strategic thinking and operational engagement. How do you feel about this dual expectation?(Required)Matrix Environment Experience(Required)Describe your experience working with multiple stakeholders and in matrix environments (e.g. reporting to a board, partnering with parallel organizations): Section 4: Connection to MissionEducational Equity & Community Impact(Required)Why are you passionate about expanding educational opportunities in communities?Connection to the Berkshires(Required)What is your connection to or interest in the Berkshire region? I currently live in the Berkshires I have lived in the Berkshires previously I have strong ties to the region (family, property, etc.) I am familiar with the region and drawn to its potential I am open to relocating for the right opportunity Please elaborate:(Required)Personal Motivation(Required)What excites you most about this Executive Director opportunity?What concerns or questions do you have about this role?(Required) Section 5: Self-ReflectionGreatest Strengths for This Role(Required)What are the top three strengths you would bring to this position?Growth Areas(Required)What are one or two areas where you would need to grow or seek support in this role?Success Definition(Required)How would you define success for yourself in the first year as Executive Director of Mill Town Charitable Foundation?Additional Information(Required)Is there anything else you would like us to know about your qualifications, experience, or fit for this role?Upload Files(Required)Upload Resume and Cover letter here. (PDF Format Only) Drop files here or Select files Accepted file types: pdf, Max. file size: 50 MB. By submitting this self-assessment and application materials, I affirm the information provided is accurate and complete to the best of my knowledge.(Required) Acknowledgment You can print a copy of your answers after you submit.
