Kaitlyn Wojtaszek
Verified Expert in Project Management
Project Manager
Dallas, TX, United States
Toptal member since January 13, 2021
Kaitlyn is an operational strategy executive with 10 years of experience unifying business functions (tech, legal, finance, ops) into cohesive and scalable organizations. A veteran in enterprise agility, she translates rigid and siloed structures into flexible operating models that balance rapid innovation with operational controls. She has a track record of driving digital transformation (HubSpot/Jira), managing $5+ million P&Ls, and leading cultural turnarounds in high-growth environments.
Project Highlights
Expertise
- Agile Leadership
- Business Transformation
- Customer Relationship Management (CRM)
- IT Project Management
- Operations
- Process Optimization
- Product Development
- Technical Project Management
Work Experience
VP of Operations and Customer Success
RecNation RV & Boat Storage
- Owned P&L and financial strategy. Managed a $5 million operating and capital budget, overseeing capital improvements and OpEx. Delivered a 15% expense reduction by restructuring labor models and introducing automated controls for capital allocation.
- Demonstrated strategic leadership and executive collaboration. Reported directly to CFO/COO as a core member of the leadership team, presenting to equity partners managing $500+ million in capital investments during monthly investor meetings.
- Handled enterprise technology transformation. Led the company's largest system migration (Zendesk to Hubspot), architected the change management strategy, and redesigned ticketing workflows and data structures to achieve cross-department integration.
- Contributed to revenue protection and collections. Reduced delinquencies by 50% through the design of a proprietary AI-powered collections tool. Automated processes resulting in improvements in bad debt recovery and cash flow velocity.
- Implemented a scalable customer success model. Managed a high-volume call center handling approximately 10,000 tickets and 4,500 calls monthly while maintaining an average Google Business rating of 4.5 stars across all facilities.
- Handled facility operations and asset management. Oversaw a comprehensive facility management program, ensuring property condition, security standards, and tenant safety across the entire portfolio.
- Managed a $3.5 million operating budget (personnel, grounds maintenance, technology) and $1.5 million capital improvement budget, delivering facility enhancements while maintaining strict fiscal discipline.
Director of Business Development
RecNation RV & Boat Storage
- Built and scaled an institutional-grade property management business serving external asset owners.
- Directed acquisition pipeline and seamless onboarding processes for new third-party managed properties.
- Established governance frameworks and facilitated regular strategic review cadences with property ownership groups.
- Enhanced operational efficiency of managed assets, reducing monthly operating expenses and improving facility quality through strategic capital improvements.
- Built and automated a comprehensive CRM system for third-party management, including an email automation pipeline, a cold outreach lead funnel program, a sales pipeline, and a customer onboarding process.
- Owned end-to-end business creation from ideation through operationalization: developed business plans and financial models, built digital presence and marketing infrastructure, negotiated vendor partnerships, implemented customer service, etc.
- Handled strategic partnership development. Cultivated high-value industry partnerships with premier brands, including Camping World, Good Sam, and Lippert, to deliver enhanced tenant amenities and services.
Chief of Staff to CEO
Q.ai - A Forbes Company
- Demonstrated cross-functional leadership and strategic execution. Directed the operations team and company-wide roadmap, ensuring the successful delivery of all product initiatives and strategic projects for the AI investment platform.
- Handled project management infrastructure. Established the enterprise project management framework: tool selection (Jira), methodology implementation (Scrum, Kanban), and standardized processes for development, testing, delivery, and go-to-market.
- Contributed to talent management and cultural development. Designed and launched comprehensive onboarding/offboarding processes, establishing clear accountability frameworks, role definitions, and cultural alignment for employees and contractors.
- Worked alongside the CEO, developed organizational optimization strategies, established MBOs and OKRs across all verticals, and implemented performance systems enabling teams to consistently achieve quarterly objectives.
- Led financial operations. Managed staff budgets, expense optimization, and subscription portfolio as a strategic partner supporting the CEO's cash management objectives.
Co-founder and COO
Moonllight Manager
- Led the creation of a fantasy soccer startup from inception to launch within three years, with it valued at $3 million. Established the vision, business model, and strategies to create a global fantasy soccer platform.
- Raised $300,000+ in capital through various instruments such as convertible notes, debt, and equity. Also, managed the company's financials and P&L.
- Acquired 12,000 subscribers to the website in just a single month of marketing (a user acquisition cost of $0.30). Experimented with various paid ad strategies across Facebook and Instagram.
Agile Transformation Lead and Change Agent
Morgan Stanley
- Drove enterprise-wide Agile transformation across a 4,000+ person technology division, serving as a strategic advisor to executive leadership during organizational redesign and operating model evolution.
- Embedded governance functions into agile delivery, aligning Legal, Risk, Compliance, and DevOps through clear operating frameworks that ensured compliance without sacrificing speed.
- Handled organizational design and transformation. Architected team structures creating autonomous working units at squad, fleet, and portfolio levels, enabling scaled agile delivery across the entire technology division.
- Contributed to performance management and reporting. Designed performance metrics and KPI frameworks for evaluating squad effectiveness and delivering executive-level insights to senior leadership.
- Contributed to organizational capability building. Developed and deployed an enterprise training curriculum encompassing advanced testing methodologies, dependency management strategies, and performance metrics.
Agile Project Manager | Scrum Master
Morgan Stanley
- Led several teams on multimillion-dollar projects (i.e., Premier Cash Management Accounts and Salesforce Integration) to produce quality, functional software for our financial advisors to better serve their high-net-worth clients.
- Demonstrated agile delivery leadership. Directed product development teams using agile methodologies (using Jira) to deliver enterprise technology solutions supporting financial advisor productivity and client experience.
- Handled process optimization. Applied agile principles and best practices to optimize team dynamics, streamline delivery processes, and maintain strategic roadmap alignment with business objectives.
Project History
Enterprise CRM Migration and Customer Operations Transformation
- 10,000+ — Monthly Ticket Volume Supported
- 30% — Reduced Average Response Time
- 25% — Improved Ticket Resolution Time
Customer care and escalation workflows were spread across fragmented legacy systems that lacked consistent data, automation, and reporting. As ticket volume grew into the thousands per month, teams struggled with visibility, inconsistent escalation handling, and manual processes that limited scalability and quality control.
I led the end-to-end migration from Zendesk to HubSpot, redesigning customer workflows, escalation paths, automation rules, and reporting dashboards. I managed change adoption across a 60-person organization while maintaining uninterrupted customer support during the transition.
Created a single source of truth for customer operations, improved speed and accountability, and enabled scale without linear headcount growth.
Third-party Property Management Business Launch
- 30% — Time to Fully Onboard and Integrate New Properties: from 60 to 45 Days
- 100% — Owner Retention Since Launch
- 3-5% — Operating Expense Variance Kept Within ±3–5% of Budget
The company identified an opportunity to manage assets for third-party owners but lacked the operational infrastructure, governance models, onboarding processes, and vendor controls needed to deliver consistent performance and earn institutional trust.
I built the third-party management platform from scratch, defining operating models, onboarding playbooks, CRM pipelines, reporting standards, and vendor performance frameworks. I partnered closely with ownership groups to align expectations and execution.
The new business created an additional revenue stream, extended institutional-grade operations to external owners, and demonstrated the scalability and reliability of the company’s operating platform.
Project Manager of a Decentralized Cryptocurrency Exchange
Launched an MVP for a high-frequency trading, decentralized, cryptocurrency exchange.
Managed a team of Toptal front-end, back-end, and solidity developers, designers, and blockchain experts to build a decentralized crypto exchange.
The business’s vision was to create a decentralized trading platform that allows for spot trading and margin trading up to 50x the leverage. The platform includes all the essential components of a trading platform, such as a price history chart (integrated with Tradeview), MetaMask wallet integration, placing a market or limit order to buy/sell assets, portfolio-related information, and transaction history. We developed an auction with an order book for users to see which orders are being placed and when they are filled for the high-frequency trading aspects. We also built a capital pool to pool together tokens for high-leverage positions and an insurance pool to mitigate any deficits on open positions.
Education
Bachelor's Degree in Computer Science
Lehigh University - Bethlehem, PA, USA
Skills
Tools
Jira, Basecamp, Sketch, Google Docs, Microsoft Excel, Google Analytics, Trello, SQL, Salesforce, Asana, GitHub, Facebook Ads Manager, Advertising Tools & Platforms, HubSpot, Canva, Atlassian
Paradigms
Agile, Agile Leadership, Agile Project Management, Scrum, Agile Product Management, Agile Delivery, Change Management, Requirements Analysis, B2C, Waterfall Delivery, Kanban, Marketplace Platforms, Management
Platforms
SharePoint, iOS, Android, WordPress, Google Ads, Zendesk
Industry Expertise
Consumer Products, Sports
Other
Outlook, PowerPoint Design, Agile Practices, IT Project Management, Scrum Master, Startups, Product Development, Product Roadmaps, Timelines, Technical Project Management, Project Timelines, Project Budget Management, Project Management, Stakeholder Management, Product Launch, Agile Coaching, Websites, Feature Backlog Prioritization, Communication, Reporting, Product Delivery, Project Delivery, Backlog Management, IT Deployments, Delivery Management, Project Discovery, Discovery Workshops, Project Scoping, Jira Administrator, Product Ownership, Estimation & Planning, Project Estimation, Project Scheduling, Product Discovery, Project Management Operations, Critical Path Analysis, Milestones, Project Planning, Workshops, Roadmaps, Product Management, Agile Transformation, Digital Project Management, Digital Innovation, Process Improvement, Process Optimization, Business Transformation, Profit & Loss (P&L), Customer Relationship Management (CRM), Finance, Fantasy Sports, Mobile, Social Media Marketing (SMM), Instagram Marketing, Mockups, Resource Allocation, Cost Estimation, Technical Requirements, Technical Leadership, Business to Consumer (B2C), Product Owner, Product Vision, Key Performance Indicators (KPIs), Risk Management, Vendor Management, Technical Analysis, Technical Business Analysis, User Stories, Scrum Product Owner Contractor, Documentation, Training Materials, APIs, Wireframe to Product, Client Relations, User Experience (UX), Front-end, Microsoft Teams, Web & Mobile Applications, Mobile Applications, Waterfall Methodology, Product Marketing, Social Media, Workshop Facilitation, Product Requirements Documentation (PRD), Go-to-market Plans, Jira Administration, Customer Success, Customer Support, Client Delivery Management, Web Marketing, Operations, Operating Models, Recruiting, Marketing Platforms, Facebook Ads, Google SEO, Social Media Strategy, Jive, Social Media Analytics, Fundraising, Financials, Pitch Decks, Computer Science, Marketing, HTML, CSS, JavaScript, Scope of Work (SOW), Scope, Prototyping, Estimations, Mobile Apps, Product Design, Coaching, Product Analytics, Writing & Editing, Cryptocurrency, Cryptocurrency Exchanges, Competitor Analysis & Profiling, GoDaddy, Yelp API, Feature Prioritization, Startup Funding, Pitch Preparation, Capital Raising, Resourcing, IT Strategy, Launch Strategy, Crypto, Decentralized Finance (DeFi), Facebook, Instagram, Local SEO, SEO Tools, Leadership, Notion, SiteLink, P&L Management, P&L Forecasting, Debt Collection, Revenue Management, Customer Retention, AI Automation, Property Management, Customer Service, Senior Executive Management, CRM, Sales, Investor Relations, Investor Presentations, Financial Management, ChatGPT, B2B Lead Generation, Branding
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