Senior Vice President, Compliance (Boston, MA)

WinnCompanies•Boston, MA

6d•$190,000 - $230,000•Hybrid

About The Position

WinnCompanies is looking for a Senior Vice President, Compliance Operations to join our team in Boston, MA. The Senior Vice President, Compliance Operations is the executive leader responsible for the day to day operations, performance, and structure of WinnResidential’s national affordable housing compliance function. This role owns the current state compliance engine – the people, processes, and delivery model that ensure accurate, timely, and consistent regulatory compliance across a large, multi state portfolio. The Senior Vice President, Compliance Operations will partner closely with the Senior Vice President, Compliance Strategy & Centralized Services who is focused on building a tech enabled, future state compliance model. While the Senior Vice President, Compliance Operations drives system modernization and workflow redesign, this role ensures that today’s operations are stable, scalable, and audit ready. If you are an executive level operator with deep affordable housing program expertise and a track record of building strong teams and systems, this is an opportunity to shape one of the largest affordable housing compliance platforms in the country. The salary range for this position is $190,000-230,000 per year dependent on experience with an annual bonus potential up for 40% of base salary. The selected candidate will adhere to the following hybrid schedule: Monday through Friday from 8:00AM to 5:00PM EST, with Monday through Thursday being in the Boston Headquarters and Fridays being remote. Responsibilities: Compliance Operations Leadership: Provide executive oversight of all day to day compliance operations nationally, ensuring accuracy, timeliness, and consistency across the portfolio. Lead a distributed team that includes Directors of Compliance, Compliance Managers, Regional Compliance Specialists/Coordinators, Certification Specialists, and support staff. Establish, monitor, and enforce performance standards for: file review quality and turnaround, recertification timeliness, rent and income limit application, resolution of findings and audit readiness Partner closely with regional operations leadership to ensure alignment, clarity of roles, and timely field support. Organizational Structure & Team Development Assess and refine the compliance organizational structure to support growth, centralization, and changing regulatory demands. Define and standardize roles, responsibilities, job ladders, and performance expectations across the compliance hierarchy. Lead workforce planning, hiring, coaching, and performance management for leaders and frontline team members. Develop and mentor emerging leaders to build a strong succession pipeline. In coloration with SVP Compliance Strategy and Centralized Services, create, implement, and manage the annual Compliance operating budget, portfolio-wide. Regulatory Excellence & Quality Assurance Serve as an executive authority on LIHTC, HUD Multifamily programs (e.g., PBRA, PBV, 202/811), HOME, and applicable state/local affordable housing programs. Oversee internal audit and quality assurance frameworks to reduce regulatory risk and improve file accuracy. Lead oversight of MORs, audits, and agency/investor reviews, including preparation, coordination, and response. Monitor evolving federal, state, and local regulations and ensure timely updates to policies, procedures, and practices. Partnership with Digital Transformation & Technology Act as the primary operational counterpart to the SVP, Compliance Strategy & Centralized Services, aligning new systems and workflow changes with real world operational needs. Support design and implementation of centralized compliance functions (e.g., reporting, recerts, file review) and tech enabled workflows. Champion adoption of new compliance tools and platforms, partnering on testing, rollout, and user training. Reporting, Communication & Cross Functional Collaboration Standardize compliance reporting across regions to ensure consistent metrics, definitions, and expectations. Set expectations for clear, professional communication between compliance, operations, clients, and internal stakeholders. Collaborate with Operations, HR, Business Intelligence, Shared Services, and Technology to clarify responsibilities and streamline processes. Use data to identify trends, risks, and improvement opportunities, and communicate those insights to senior leadership and clients. Performance Management & Continuous Improvement Own key compliance performance indicators and drive continuous improvement initiatives to improve accuracy, speed, and service. Identify and address structural gaps (e.g., training needs, process bottlenecks, resource constraints) that impede performance. Promote a culture of accountability, service, and excellence within the compliance organization. Requirements: 12+ years of progressive experience in affordable housing compliance, property management operations, or closely related fields. Significant leadership experience overseeing multi state, multi program affordable housing portfolios. Deep expertise in LIHTC and HUD Multifamily programs, with strong familiarity with layered financing and state/local program requirements. Demonstrated success building and leading high performing teams through change, growth, and operational transformation. Proven ability to develop and implement standardized processes, operating models, and performance management systems. Exceptional communication, relationship building, and influencing skills, including the ability to partner effectively with executive leadership, regional operators, clients, and regulators. Preferred Qualifications: Experience implementing centralized compliance functions and/or tech enabled workflow redesign. Executive experience in a large affordable housing or multifamily management company. Prior responsibility for national or large multi region compliance operations.

Requirements

12+ years of progressive experience in affordable housing compliance, property management operations, or closely related fields.
Significant leadership experience overseeing multi state, multi program affordable housing portfolios.
Deep expertise in LIHTC and HUD Multifamily programs, with strong familiarity with layered financing and state/local program requirements.
Demonstrated success building and leading high performing teams through change, growth, and operational transformation.
Proven ability to develop and implement standardized processes, operating models, and performance management systems.
Exceptional communication, relationship building, and influencing skills, including the ability to partner effectively with executive leadership, regional operators, clients, and regulators.

Nice To Haves

Experience implementing centralized compliance functions and/or tech enabled workflow redesign.
Executive experience in a large affordable housing or multifamily management company.
Prior responsibility for national or large multi region compliance operations.

Responsibilities

Provide executive oversight of all day to day compliance operations nationally, ensuring accuracy, timeliness, and consistency across the portfolio.
Lead a distributed team that includes Directors of Compliance, Compliance Managers, Regional Compliance Specialists/Coordinators, Certification Specialists, and support staff.
Establish, monitor, and enforce performance standards for: file review quality and turnaround, recertification timeliness, rent and income limit application, resolution of findings and audit readiness
Partner closely with regional operations leadership to ensure alignment, clarity of roles, and timely field support.
Assess and refine the compliance organizational structure to support growth, centralization, and changing regulatory demands.
Define and standardize roles, responsibilities, job ladders, and performance expectations across the compliance hierarchy.
Lead workforce planning, hiring, coaching, and performance management for leaders and frontline team members.
Develop and mentor emerging leaders to build a strong succession pipeline.
Serve as an executive authority on LIHTC, HUD Multifamily programs (e.g., PBRA, PBV, 202/811), HOME, and applicable state/local affordable housing programs.
Oversee internal audit and quality assurance frameworks to reduce regulatory risk and improve file accuracy.
Lead oversight of MORs, audits, and agency/investor reviews, including preparation, coordination, and response.
Monitor evolving federal, state, and local regulations and ensure timely updates to policies, procedures, and practices.
Act as the primary operational counterpart to the SVP, Compliance Strategy & Centralized Services, aligning new systems and workflow changes with real world operational needs.
Support design and implementation of centralized compliance functions (e.g., reporting, recerts, file review) and tech enabled workflows.
Champion adoption of new compliance tools and platforms, partnering on testing, rollout, and user training.
Standardize compliance reporting across regions to ensure consistent metrics, definitions, and expectations.
Set expectations for clear, professional communication between compliance, operations, clients, and internal stakeholders.
Collaborate with Operations, HR, Business Intelligence, Shared Services, and Technology to clarify responsibilities and streamline processes.
Use data to identify trends, risks, and improvement opportunities, and communicate those insights to senior leadership and clients.
Own key compliance performance indicators and drive continuous improvement initiatives to improve accuracy, speed, and service.
Identify and address structural gaps (e.g., training needs, process bottlenecks, resource constraints) that impede performance.
Promote a culture of accountability, service, and excellence within the compliance organization.