Drew Oswald
St. Paul,USA
Summary
Highly skilled product management leader with experience leading long term product strategy, building strong cross department relationships and delivering market leading products across multiple industries.
Overview
14
14
years of professional experience
1
1
Certification
Work History
Principal Product Manager
Procore
04.2025 - Current
- Mentor PMs and influence product strategy across adjacent product areas and platform initiatives.
- Partner with GTM teams to drive business outcomes, customer adoption and monetization strategy.
- Lead market analysis efforts into new markets, verticals and customer types.
- Analyze and investigate product metrics and financials to continue driving ARR and adoption improvement
Senior Product Manager
Procore
06.2022 - 04.2025
- Spearhead the product strategy and roadmap for Procore’s Bidding platform, delivering incremental and major releases over a 3 year period.
- Uncovered monetization opportunity on legacy SKUs; led initiative to convert unpaid Bidding users to paid plans, resulting in $2M+ ARR uplift with minimal churn.
- Led 150% increase in annual recurring revenue for Bidding product line by delivering high-impact features, tightening product-market alignment, and partnering on monetization strategy.
- Led the strategic transition of Bidding from a standalone growth product to a core component of Procore’s enterprise platform, enabling deeper integration, cross-product value, and improved positioning for large-scale customers.
Senior Product Manager
divvyDOSE
05.2021 - 06.2022
- Responsible for building and launching divvyDOSE’s online customer enrollment product, the first customer facing product at the company.
- Selected Contributions:
- Led research and planning efforts to launch a new digital enrollment product at divvyDOSE.
- Increased customer conversion rates by 2x compared to previous enrollment method.
- Partnered with research team to conduct both attitudinal and usability tests to inform approach and strategy for the product.
- Delivered on product goals to increase customer enrollment and decrease overall enrollment cost, providing top and bottom-line savings to the company.
Group Product Manager
Unanet
01.2021 - 05.2021
- Led the Product Management organization for Unanet’s second largest product line.
- Selected Contributions:
- Introduced and launched customer suggestion portal to drive customer interaction and market validation.
- Built strategy to enable sales growth through new channels and to drive existing customer retention.
- Managed and mentored a team of product managers and technical writers to deliver world class software to clients
Senior Manager of Product Management
Accruent
10.2020 - 01.2021
- Responsible for a product portfolio with over $30M in ARR, including the entire product lifecycle from new market analysis to product end of life and profitability.
- Selected Contributions:
- Managed a team of 3 product managers to drive the long-term strategy of 4 individual products within an overall product line.
- Led market analysis and product investment decisions based on market viability, competitive gaps and long term profitability
- Built ongoing processes and systems to consistently generate intelligence from win/loss calls, customer interviews, competitive analysis and market research
Product Manager
Accruent
01.2018 - 01.2019
- Product Manager for one of Accruent’s highest revenue products, helping customers around the globe solve their facilities and maintenance problems.
- Selected Contributions:
- Developed and executed long term product roadmap to defend existing market segments and grow into new and development market segments.
- Organized and led inaugural Customer Advisory Board to build relationships and solicit input from key customers
Product Owner
Calabrio
05.2016 - 12.2017
- Product Owner for Calabrio’s Analytics product, providing applied and predictive analytics solutions to customers and users across all industries
- Selected Contributions:
- Responsible for delivering on Calabrio’s strategic roadmap by distilling customer and market feedback into clear requirements for engineers.
- Conducted all Agile ceremonies, including standups, planning, retrospectives and quarterly planning.
- Led a long-term discovery and execution of a complete UI/UX overhaul.
Technical Product Manager
CLEAResult
09.2014 - 05.2016
- Product Manager for CLEAResult’s largest technology product responsible for $200M in transactions on annual basis
- Selected Contributions:
- Responsible for setting the long term vision and strategy of the product and communicating it to internal and external stakeholders
- Partnered with UX to redesign key aspects of product, leading to 86% increase in customer satisfaction
Business Analyst
CLEAResult
10.2013 - 09.2014
Project Analyst
CLEAResult
08.2012 - 10.2013
Energy & Sustainability Specialist
Shaw Environmental
05.2011 - 08.2012
Education
Bachelor of Arts - Environmental Studies
Beloit College
Beloit, WI05.2011
Skills
- Product Strategy
- Go to Market Planning
- Market Analysis
- Product Economics/Pricing
- Customer Interviews
- Stakeholder Management
- Competitive intelligence
- Stakeholder management
- Business case development
- Pricing strategy
Certification
Pragmatic Marketing Certified
Timeline
Principal Product Manager
Procore
04.2025 - Current
Senior Product Manager
Procore
06.2022 - 04.2025
Senior Product Manager
divvyDOSE
05.2021 - 06.2022
Group Product Manager
Unanet
01.2021 - 05.2021
Senior Manager of Product Management
Accruent
10.2020 - 01.2021
Product Manager
Accruent
01.2018 - 01.2019
Product Owner
Calabrio
05.2016 - 12.2017
Technical Product Manager
CLEAResult
09.2014 - 05.2016
Business Analyst
CLEAResult
10.2013 - 09.2014
Project Analyst
CLEAResult
08.2012 - 10.2013
Energy & Sustainability Specialist
Shaw Environmental
05.2011 - 08.2012
Bachelor of Arts - Environmental Studies
Beloit College
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