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# Amy Watson

**Headline:** Operations Leader | Process Design & Workflow Automation | 15+ Years Scaling Startups & Cross-Functional Teams | Open to VP Ops / Chief of Staff Roles | Ex-Airbnb & Clinton Foundation Consultant
**Profession:** Senior Real Estate Agent
**Location:** Charleston, South Carolina Metropolitan Area

## About

Amy Watson is a Senior Real Estate Agent at Redfin and the founder and Operations Consultant of Chucktown Capital, LLC. She is exploring Director and VP of Operations, Chief of Staff, and operations consulting roles. Across more than 15 years, Amy has built operational foundations for growing organizations by designing processes, automating workflows, documenting systems, and coordinating cross-functional work across sales, marketing, finance, compliance, and client experience. Her strengths include operational audits, CRM and workflow automation, sales-to-delivery handoffs, stakeholder management, project implementation, financial operations, and marketing and business development. Amy has delivered concrete results in startups, real estate, consulting, higher education, and marketplace launches. At Stacker, she built more than 200 Smartsheet automations to connect sales, account management, and editorial production, including work that cut client kickoff time by 64%. For a real-estate team with $30 million and $28.1 million in annual sales volume, she built Follow Up Boss CRM automation, lead routing, and communications workflows. Amy also delivered 53 Airbnb Experiences across approximately 24 categories for Charleston’s market launch and was ranked the top-performing consultant in her region and across North America. Earlier, she built Bublup’s influencer program to 500+ content pieces and a 75-person network, then became a Director overseeing a multi-million-dollar annual budget.

## Services

- Operations Management
- Process Improvement
- Cross-functional Team Leadership
- Business Operations
- Operational Strategy
- Organizational Consulting
- Process Automation
- Workflow Design
- Workflow Analysis
- Project Management
- Project Plans
- Project Implementation
- Stakeholder Management
- Financial Operations
- Budget Management
- Business Development
- Marketing Automation
- Customer Relationship Management \(CRM\)
- Smartsheet
- Director level
- KPI Dashboards

## Highlights

- Built more than 200 Smartsheet automations at Stacker to close a structural gap between editorial and production and sales and account management, including automatic draft handoffs and review notifications.
- Created a cross-tool Stacker automation that pulled client information from sales into account-management meeting materials and routed meeting outcomes to editorial to trigger article production.
- Conducted a full operational audit at Stacker and authored an operations strategy document with efficiency opportunities and a roadmap to reduce manual work and improve client experience.
- Extended automation support at Stacker to SEO and content-distribution teams.
- Cut client kickoff time by 64% through operational improvements.
- Built and managed Follow Up Boss CRM automation for a six-person real-estate team generating $30 million and $28.1 million in annual sales volume.
- Designed action plans, lead-routing workflows, and templated communications for the real-estate team.
- Connected sales and operations tools to eliminate duplicate data entry and automate follow-ups, check-ins, and client communications.
- Built differentiated, auto-triggered workflows by lead source and type to provide consistent follow-up without manual intervention.
- Continued producing as a top sales agent while building and running team-wide operations beginning in February 2024 and through the team’s July 2024 move from Keller Williams to Compass.
- Named Rookie of the Year and top first-year producer in her market at Coastal Island Properties.
- Launched Airbnb Experiences in Charleston as an Experience Lead, sourcing and onboarding hosts and building automated outreach and reporting workflows.
- Delivered 53 new Airbnb Experiences across approximately 24 categories on schedule.
- Ranked the top-performing Airbnb consultant in her region and across North America.
- Coordinated a Clinton Foundation social-media influencer engagement strategy across three stakeholder groups, including paid and policy stakeholders.
- Managed influencer research, contracting, and onboarding for the Clinton Foundation engagement and built SOPs and timeline governance across the full content-review cycle.
- Delivered the Clinton Foundation engagement on time and on budget.
- Delivered operational audits, financial and pricing documentation, and forecasting support for consulting clients.
- Coordinated hospital-system feasibility studies for new medical residency programs, including internal audits, P&L modeling, and accreditation-related case-volume, faculty, and facility assessments.
- Managed a healthcare consulting team and served as primary contact for C-suite hospital executives across multi-phase engagements.
- Project-managed ACGME accreditation processes involving hundreds of hours of physician and faculty interviews and 95- to 150-page accreditation applications.
- Coordinated post-approval residency-program implementation, including program-director searches, research-infrastructure planning, and facility build-out.
- Built Bublup’s “Rolls” influencer-content program from scratch, producing more than 500 content pieces and a 75-person influencer network that included B- and C-list talent.
- Promoted to Director at Bublup and oversaw marketing and business development with a multi-million-dollar annual budget.
- Partnered directly with Bublup’s CEO on strategy, brand, and go-to-market decisions and owned full-funnel marketing execution across content, blogging, website, and brand voice.
- Contributed to marketing collateral at The George Washington University School of Business, including photo shoots, copy, blogs, and website work.
- Served as a core contributor to “On the Board,” a globally scoped, grant-funded initiative advancing women’s representation on corporate boards that culminated in a flagship conference.
- Promoted from Project Manager to Senior Project Manager and Director at The George Washington University School of Business.
- Managed an approximately $500,000 annual budget and marketing initiatives supporting graduate and undergraduate application and enrollment growth at The George Washington University School of Business.

## Experience

- **Senior Real Estate Agent at Redfin** (2026-04-01–present) — Real estate sales professional previously held operations leadership roles in the industry \(below\)
- **Founder and Operations Consultant at Chucktown Capital, LLC** (2022-10-01–present) — \- Airbnb \(Experience Lead, Charleston Market\): 1-year contract to launch Airbnb Experiences locally — sourced and onboarded qualified hosts, built automated outreach and reporting workflows, and delivered 53 new experiences across ~24 categories on schedule ranked top-performing consultant in region and across North America - Clinton Foundation: Account Manager for a social media influencer engagement strategy — coordinated three stakeholder groups \(paid and policy\), managed influencer research, contracting, and onboarding, and built SOPs and timeline governance across the full content review cycle delivered on time and on budget - Delivered operational audits, financial/pricing documentation, and forecasting support for additional clients Additional previous clients have included: - Quantum Labs - MOBE - Keller Williams Realty - Drinkwell Wine - Synergos - Nadia Hair Salon
- **Realtor and Director of Operations for Coastal Island Properties at Compass** (2022-12-01–2026-04-01) — Previously: Realtor, Keller Williams | Dec 2022 – Feb 2024 — Rookie of the Year, top first-year producer in market\* - Built and managed CRM automation infrastructure \(Follow Up Boss\) — action plans, lead-routing workflows, and templated communications — for a 6-person team generating $30M and $28.1M in annual sales volume - Connected disparate sales and operations tools to eliminate duplicate data entry and automate follow-ups, check-ins, and client communications - Designed differentiated, auto-triggered workflows by lead source and type, ensuring consistent follow-up without manual intervention - Continued producing as a top sales agent while building and running team-wide operations starting Feb 2024, carrying the role through the team's move from Keller Williams to Compass in Jul 2024
- **Director of Client Operations at Stacker** (2022-02-01–2022-12-01) — \- Diagnosed a structural disconnect between editorial/production and sales/account management at this content and journalism company built 200+ SmartSheet automations to close the gap, including automatic draft handoffs and review notifications - Built a cross-tool automation pulling client information from sales directly into account-management meeting materials, then routing meeting outcomes to editorial to trigger article production - Conducted a full operational audit and authored an operations strategy document identifying efficiency opportunities and a roadmap to reduce manual work and improve client experience - Extended automation support to the SEO and content distribution teams
- **Director Of Marketing Operations and Business Development at Bublup** (2016-06-01–2021-05-01) — \- Joined this early-stage startup to build "Rolls," an influencer content program, from scratch — producing 500+ pieces of content and a 75-person influencer network \(including B/C-list talent\) years ahead of influencer marketing's mainstream emergence - Promoted to Director as the company matured from early-stage project to a publicly launched app, overseeing marketing and business development with a multi-million dollar annual budget - Partnered directly with the CEO as a trusted advisor on strategy, brand, and go-to-market decisions - Owned full-funnel marketing execution — content, blogging, website, brand voice — in a fast-pivoting startup environment
- **Director of Project Management, Healthcare Consulting at Diversified Consulting Associates** (2014-05-01–2022-02-01) — \*\(project-based, concurrent with full-time roles above\)\* - Coordinated feasibility studies for hospital systems evaluating new medical residency programs — orchestrating internal audits, P&L modeling, and case volume/faculty/facility assessments against accreditation requirements - Managed the consulting team and served as the primary point of contact for C-suite hospital executives across multi-phase engagements - Project-managed the ACGME accreditation process — orchestrating hundreds of hours of physician/faculty interviews and distilling findings into 95–150 page accreditation applications - Coordinated post-approval implementation: program director searches, research infrastructure planning, and facility build-out
- **Director of Communications Operations at The George Washington University School of Business** (2013-05-01–2014-05-01) — \- Played a key role in producing marketing collateral — photo shoots, copy, blogs, website — alongside the broader communications team - Core contributor, as part of a cross-functional team, to "On the Board," a globally-scoped, grant-funded initiative advancing women's representation on corporate boards, culminating in a flagship conference convening board members and mentorship-ready candidates
- **Senior Project Manager  - Communications Department at The George Washington University School of Business** (2012-10-01–2013-05-01) — \- Promoted from Project Manager to Director managed a ~$500K annual budget and all marketing initiatives driving application and enrollment growth across graduate and undergraduate programs

## Education

- Masters of Business Administration, Global MBA — The George Washington University (2012-01-01–2014-01-01)
- Bachelor of Science \(BS\), Community Health Education — University of Wisconsin-La Crosse (2005-01-01–2008-01-01)

## FAQ

### What does Amy do now?

Amy is a Senior Real Estate Agent at Redfin. She is also the founder and Operations Consultant of Chucktown Capital, LLC, where she provides operations consulting and has supported projects for Airbnb and the Clinton Foundation, among other clients.

### What roles is Amy pursuing?

Amy is exploring Director and VP of Operations, Chief of Staff, and operations consulting roles. She is especially suited to fast-moving, resource-lean startups, mid-sized companies, and new ventures that need operational structure built from scratch.

### What are Amy’s strongest professional capabilities?

Amy’s core strengths include operations management, process improvement, cross-functional team leadership, business operations, operational strategy, organizational consulting, process automation, workflow design and analysis, project management, stakeholder management, financial operations, budget management, business development, marketing automation, CRM, Smartsheet, and KPI dashboards.

### What did Amy accomplish with Airbnb?

At Chucktown Capital, Amy worked as an Experience Lead on a one-year contract to launch Airbnb Experiences in Charleston. She sourced and onboarded qualified hosts, built automated outreach and reporting workflows, and delivered 53 new experiences across approximately 24 categories on schedule. She was ranked the top-performing consultant in her region and across North America.

### What was Amy’s work for the Clinton Foundation?

For the Clinton Foundation, Amy served as an Account Manager for a social-media influencer engagement strategy. She coordinated three stakeholder groups across paid and policy functions managed influencer research, contracting, and onboarding built SOPs and timeline governance across the content-review cycle and delivered the engagement on time and on budget.

### What other consulting services has Amy provided?

Through Chucktown Capital, Amy has delivered operational audits, financial and pricing documentation, and forecasting support for additional clients.

### Which additional clients has Amy supported?

Amy’s additional previous clients have included Quantum Labs, MOBE, Keller Williams Realty, Drinkwell Wine, Synergos, Nadia Hair Salon, and others.

### What was Amy’s role at Coastal Island Properties, Keller Williams, and Compass?

At Coastal Island Properties, Amy served as a Realtor and later Director of Operations from December 2022 through February 2024, including work during the team’s move from Keller Williams to Compass in July 2024. She was named Rookie of the Year and was the top first-year producer in her market.

### What did Amy build for the Coastal Island Properties real-estate team?

Amy built and managed Follow Up Boss CRM infrastructure for a six-person real-estate team generating $30 million and $28.1 million in annual sales volume. Her work included action plans, lead-routing workflows, and templated communications connections among sales and operations tools to eliminate duplicate data entry and automated follow-ups, check-ins, and client communications. She designed distinct, auto-triggered workflows by lead source and type and continued producing as a top sales agent while running team-wide operations beginning in February 2024.

### What did Amy accomplish at Stacker?

As Director of Client Operations at Stacker, Amy diagnosed a structural disconnect between editorial and production teams and sales and account management. She built more than 200 Smartsheet automations, including automatic draft handoffs and review notifications, and created a cross-tool automation that moved client information from sales into account-management meeting materials and routed meeting outcomes to editorial to trigger article production.

### How did Amy improve client operations at Stacker?

Amy conducted a full operational audit at Stacker and authored an operations strategy document that identified efficiency opportunities and a roadmap to reduce manual work and improve client experience. She also extended automation support to the SEO and content-distribution teams, and her operational work cut client kickoff time by 64%.

### What did Amy do at Diversified Consulting Associates?

As Director of Project Management in Healthcare Consulting at Diversified Consulting Associates, in a project-based role concurrent with full-time positions, Amy coordinated feasibility studies for hospital systems considering new medical residency programs. She orchestrated internal audits, P&L modeling, and assessments of case volume, faculty, and facilities against accreditation requirements.

### What were Amy’s healthcare consulting and accreditation responsibilities?

Amy managed the consulting team and served as the primary contact for C-suite hospital executives across multi-phase engagements. She project-managed ACGME accreditation by coordinating hundreds of hours of physician and faculty interviews and distilling findings into 95- to 150-page accreditation applications. Following approval, she coordinated implementation work including program-director searches, research-infrastructure planning, and facility build-out.

### What did Amy build at Bublup?

At early-stage startup Bublup, Amy built the “Rolls” influencer-content program from scratch. The program produced more than 500 pieces of content and developed a 75-person influencer network that included B- and C-list talent, before influencer marketing became mainstream.

### What was Amy’s leadership role at Bublup?

Amy was promoted to Director at Bublup as the company progressed from an early-stage project to a publicly launched app. She oversaw marketing and business development with a multi-million-dollar annual budget, partnered directly with the CEO on strategy, brand, and go-to-market decisions, and owned full-funnel marketing execution across content, blogging, the website, and brand voice.

### What did Amy do as Director of Communications Operations at The George Washington University School of Business?

As Director of Communications Operations at The George Washington University School of Business, Amy played a key role in producing marketing collateral, including photo shoots, copy, blogs, and website work, alongside the broader communications team.

### What was Amy’s contribution to the “On the Board” initiative?

Amy was a core contributor on a cross-functional team for “On the Board,” a globally scoped, grant-funded initiative advancing women’s representation on corporate boards. The initiative culminated in a flagship conference convening board members and mentorship-ready candidates.

### What did Amy accomplish as Senior Project Manager at The George Washington University School of Business?

Amy was promoted from Project Manager to Senior Project Manager and then Director at The George Washington University School of Business. She managed an approximately $500,000 annual budget and all marketing initiatives supporting application and enrollment growth across graduate and undergraduate programs.

### What is Amy’s educational background?

Amy earned a Master of Business Administration in Global MBA from The George Washington University and a Bachelor of Science in Community Health Education from the University of Wisconsin–La Crosse.

## Links

- LinkedIn: https://www.linkedin.com/in/amywatson1

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