Olga McCaffrey

As one of the first four tech hires at Lessen, I had the unique opportunity of innovating, designing, and building the Lessen product suite from the ground up. After implementing the platform foundation, setting the overall product vision, and defining the tech org processes for the product, engineering, design, and QA teams, I moved on to own the entire suite of products related to generating revenue for Lessen through the intake and completion of jobs.

• The product suite I innovated across the Lessen platform allowed our operations and field teams to completely move off of spreadsheets and manage jobs, vendors, materials, income, and costs, in a streamlined, accurate, and scalable way, which allowed Lessen to expand into almost every major metro area in the US and grow our client-base by 60%.
• I managed a team of six engineers through group leadership and 1:1 coaching. My mentorship to the engineers helped them develop customer empathy, product ownership/accountability, improved estimation (based on complexity and velocity calculations for ICs), and grow their individual skill sets in order to enable them achieve their personal and professional goals. Two of my engineers went on to become tech leads and one was put on the engineering management path as a direct result of the coaching/mentorship I provided.
• In and effort to introduce Agile methodology to allow our teams to operate effectively, I introduced industry-standard tools and defined processes for the entire tech org. This allowed each team to maintain a high level of organization through the use of business requirement documentation, engineering design docs, roadmap planning, and product launch plans, while maintaining consistency throughout the entire lifecycle of each feature.

As a Senior Product Manager, I developed a roadmap and vision for our full product suite to align to the company’s OKRs, worked closely with engineering leaders to develop new team structures, introduce agile and scrum methodology, and set processes in place to ensure that both the product and engineering teams were set up for success and could confidently attain the roadmap goals.

As Senior Product Manager on the Data Team, I worked closely with backend and data engineers, along with data scientists to solve customer pain points in a data-driven way. During my time at Keap, I drove and owned several products including, Recommendations API, Smart Lists, Accurate Email History, Delinquent Email Management, and SMS Automation. I also drove the initiative to re-architect our data infrastructure and data platform to allow the business to maintain data structure and integrity at scale in a cost-efficient and secure way.

• I worked with the team on improving our sprint capacity planning and organization to create consistency in our deliverables while accounting for tech debt and sprint interruptions. When I joined the Data Team, they were hitting around 65% of their sprint commitment goal, after one month of being on the team, we began delivering at 100% and higher toward our sprint commitment.
• In an effort to improve proactivity and address issues before they become a customer concern, implemented monitoring and alerting to our pipelines and data flow jobs. We also built monitoring dashboards for all client-facing initiatives that the team worked on to ensure we had visibility into performance in order to address issues and make data-driven decisions to quickly pivot and provide the best possible experience to our customers. We also added simulations pre-launch to understand expected feature behavior and identify any gaps/issues that needed to be addressed prior to launch.
• To help our customers increase engagement and improve deliverability of their email marketing campaigns, we created ML-driven aggregate lists of contacts with recommended actions to include in email broadcasts based on the desired outcomes of our customers. Through the use of Smart Lists, we saw email engagement go up by 35% on avg per broadcast, and significantly improved email deliverability by enabling customers to clean up 25k + delinquent emails in one day, decrease email domain typos, and exclude high-risk contacts from their broadcasts.

As Senior Product Manager, I reported to the CTO and directly managed a team of engineers and data scientists, acting as both a senior product manager and engineering manager. I owned all of the data & reporting products and innovated an employee engagement product for restaurant franchises. I implemented a product plan, product strategy, and roadmap for all of the company's product offerings, which enabled us to scale our products, use financial forecasting, and prioritize features in a data-driven way.

As one of three members of the company’s leadership team, my role focused on overseeing and managing all advertising operations, providing thought-leadership and a vision for company growth, leading and mentoring employees, and owning the evolution and vision of the product.

• Focused teams on developing innovative and cutting-edge approaches at all levels with effective resource allocation and strategic planning.
• Created annual budget and developed comprehensive plan to accomplish company objectives while staying within budget.
• Optimized operational processes by developing company-wide analytics tool to address client-specific metrics.

AdIQ was a programmatic concept that I created with my partner and launched with a small team of employees. We envisioned a platform that incorporated a custom attribution modeling system to allow for additional insight on user behavior to allow for optimizations focused on driving results and eliminating the guesswork out of programmatic advertising. At AdIQ I directly managed all of our employees, oversaw the design and development of our platform, and directly managed all customer relationships and advertising campaigns.