Maggie Bouscaren
Business Strategy & Monetization Leader | B2B AI, API & SaaS Platforms | Platform Economics & Operating Models
San Francisco, California, United States of America
Business Strategy & Monetization Leader | B2B AI, API & SaaS Platforms | Platform Economics & Operating Models
San Francisco, California, United States of America
Work history
Plaid
Docusign
Asutra
ClearRock Capital (Acquired by Mercer Advisors)
Mercer Advisors
Bank of America Merrill Lynch
Vanderbilt Owen Graduate School of Management
SEP 2024 - PRESENT · 2.1 years
Head of Monetization Strategy
SEP 2024 - PRESENT · 2.1 years
• Designed and delivered phased strategy for top company-wide priority on margin protection, balancing near-term cost recovery against rising costs with long-term pricing durability; drove C-suite alignment on key levers • Delivered +2.4% incremental top-line and +13.5% operating profits via pricing governance overhaul: consolidated 60+ discount approval matrices into 4, raising new business ASPs 7.4% and reducing revenue-weighted renewal discounts from 7.5% to 1.2% • Launched novel, alternative price metric and bundling strategies delivering $5M+ incremental ACV within months, including competitive wins for marquee customers • Redesigned product commercialization process end-to-end, establishing product launch readiness criteria, pricing and packaging approval workflows, SKU governance, and cross-functional roles and responsibilities across product, GTM, and finance; enabled 20+ product launches balancing speed with rigorous pricing standards, clean billing, and GTM efficiency • Scaled CI function, delivering high-priority GTM battlecards, product tear-downs and live deal support
Head of Pricing Strategy
SEP 2024 - PRESENT · 2.1 years
Developing and executing product monetization strategies to drive reach and revenue, deliver unique customer value, and differentiate from the competition, in line with company goals.
JAN 2018 - SEP 2024 · 6.8 years
Director, Monetization Strategy
MAY 2022 - SEP 2024 · 2.4 years
• Led monetization strategy for DocuSign's AI-driven transformation as core member of cross-functional Growth Strategy Tiger Team; modeled AI margin trade-offs, compute utilization, and segment migration velocity to secure exec. sign-off • Developed 3+ year monetization vision targeting >$10B revenue including first company-wide pricing roadmap; regular C-suite presenter on P&P strategy and growth investment trade-offs • Designed and executed global price-model transformations via A/B testing across self-serve (PLG) and enterprise channels; boosted core product usage 60%, improved close rates 9%, shortened sales cycles 2 days, reduced churn 9%; work informed foundational monetization architecture for next-gen platform products • Led feature gating and model tiering strategy across 15+ product innovations, including the fastest-selling add-on in company history • Conceived and led cross-functional execution of largest revenue acceleration in company history: multi-product bundle program generating double-digits incremental annualized revenue in under one quarter, 2x-ing multi-product attach rate YoY and increasing avg. new customer deal size 20% • Developed cross-sell and retention sales plays, including pricing collateral that remains among the most-referenced assets across the global field org. • Team lead and people manager (team of 8); accelerated promotion path
Senior Manager, Monetization Strategy
AUG 2020 - MAY 2022 · 1.8 years
• Pricing and packaging strategy lead for core e-signature product and adjacent product add-ons • Developed business case and designed monetization strategy for 15+ new product innovations, including what became the fastest selling add-on in company history, surpassing add-on attach rate goals and reaching more customers than any new innovation previously; successfully gained c-level support despite initial skepticism for direct monetization strategy • Implemented first of their kind, and since repeated, price promotions directly resulting in $XXXk GNMRR in quarter • Conducted customer research to directly inform pricing and packaging strategies of new and existing innovation, competitive strategy, and product roadmap and investment, including: qualitative in-depth interviews, quantitative studies including conjoint analysis, Van Westendorp and Gabor-Granger price sensitivity meters; managed multiple engagements and relationships with 3rd-party vendors including pricing and market research consultancies • Worked extensively with Product Development and Product Design over 18+ mo. period to develop the first-ever offering that allows two businesses to collaborate and execute an agreement for their mutual end client; new innovation was purchased and adopted by a top 5 customer within first year and resulted in 3 patents (US20220245592A1 · Filed Jan 29, 2021, US20220245201A1 · Filed Jan 29, 2021, US20220245122A1 · Filed Jan 29, 2021) • First female patent recipient at DocuSign (and only Pricing Strategy team member)
Senior Monetization Strategy Manager
AUG 2020 - MAY 2022 · 1.8 years
• Pricing and packaging strategy lead for core e-signature product and adjacent product add-ons • Developed business case and designed monetization strategy for 15+ new product innovations, including what became the fastest selling add-on in company history, surpassing add-on attach rate goals and reaching more customers than any new innovation previously; successfully gained c-level support despite initial skepticism for direct monetization strategy • Implemented first of their kind, and since repeated, price promotions directly resulting in $XXXk GNMRR in quarter • Conducted customer research to directly inform pricing and packaging strategies of new and existing innovation, competitive strategy, and product roadmap and investment, including: qualitative in-depth interviews, quantitative studies including conjoint analysis, Van Westendorp and Gabor-Granger price sensitivity meters; managed multiple engagements and relationships with 3rd-party vendors including pricing and market research consultancies • Worked extensively with Product Development and Product Design over 18+ mo. period to develop the first-ever offering that allows two businesses to collaborate and execute an agreement for their mutual end client; new innovation was purchased and adopted by a top 5 customer within first year and resulted in 3 patents (US20220245592A1 · Filed Jan 29, 2021, US20220245201A1 · Filed Jan 29, 2021, US20220245122A1 · Filed Jan 29, 2021) • First female patent recipient at DocuSign (and only Pricing Strategy team member)
Manager, Monetization Strategy
AUG 2019 - AUG 2020 · 1.1 years
• Pricing lead for core e-signature product, working across the product organization to develop software product pricing and packaging strategies that drive growth, deliver competitive differentiation, and consider company margin targets • Directly supported our worldwide field organization (AEs, RMs, CSMs, SE/SCs) on all pricing and packaging related topics; proactively developed key Sales assets that continue to be among the most used Sales assets at the company today • Repeatedly developed business cases for new and existing innovation to present to c-suite, including detailed monetization strategy and financial modeling Previously in a Corporate Strategy role where I: • Partnered with the Product org. to reshape the product development process, team, and prioritization to incorporate customer insights and company-level strategy
Monetization Strategy Manager
AUG 2019 - AUG 2020 · 1.1 years
• Pricing lead for core e-signature product, working across the product organization to develop software product pricing and packaging strategies that drive growth, deliver competitive differentiation, and consider company margin targets • Directly supported our worldwide field organization (AEs, RMs, CSMs, SE/SCs) on all pricing and packaging related topics; proactively developed key Sales assets that continue to be among the most used Sales assets at the company today • Repeatedly developed business cases for new and existing innovation to present to c-suite, including detailed monetization strategy and financial modeling
Corporate Strategy
JAN 2018 - DEC 2018 · 1 year
• Designed new premium package, leveraging existing features to command higher price point and differentiate from competition; presented to CEO and C-suite to receive approval for 2019 launch • Reshaped product development process and team to incorporate strategy and customer insights to guide FY20 core product roadmap; presented and facilitated workshop at annual PM offsite • Conducted and synthesized 20+ cross-functional interviews to prioritize and structure product development
JAN 2018 - DEC 2018 · 1 year
Strategy & Marketing
JAN 2018 - DEC 2018 · 1 year
• Developed multi-channel marketing strategy for ecommerce startup; managed several marketing campaigns resulting in the largest single day of sales ever at the time • Analyzed historical transactional data and conducted customer survey to segment customers by their purchasing behavior, detect drivers of customer loyalty, and inform new marketing positioning for company rebrand • Identified opportunity to improve operations, increasing throughput by 50%
JAN 2014 - DEC 2017 · 4 years
Director of Business Development & Marketing
JAN 2014 - DEC 2017 · 4 years
• Designed and executed comprehensive growth strategy for independent, SEC-registered investment advisory boutique, launching new sales and operations initiatives to increase lead generation by 500%, achieve XX% compound annual asset growth, and increase average client assets by XX%+ • Developed and tracked KPIs across functional areas, institutionalizing quarterly performance report to identify operational improvements and inform short- and long-term strategic goals • Created and implement first-ever internal business development challenge with 100% participation rate, resulting in conversion of firm’s largest private client at the time • Led operations meetings; created CRM workflow automation and live dashboards to streamline processes • Managed ~$XM in investments as lead Financial Advisor develop for multiple families
JAN 2014 - DEC 2017 · 4 years
Director of Business Development & Marketing for ClearRock Capital (acq. by Mercer)
JAN 2014 - DEC 2017 · 4 years
(Prior to the successful acquisition by Mercer Advisors) • Designed and executed go-to-market strategy achieving 11.9% compound annual asset growth; directly responsible for managing ~$5M in private client investments; built 0 → 1 internal performance reporting for execs
JAN 2011 - DEC 2014 · 4 years
Investment Banking Analyst
JAN 2012 - DEC 2014 · 3 years
• Executed $293B in 35+ equity transactions in U.S. and LatAm exchanges, including $1.5B ING U.S. IPO, $2.5B Grupo Financiero Banorte follow-on, and 1st overnight-marketed offering in Mexico ($214M OMA Airports)
Investment Banking Analyst - Equity Capital Markets
JAN 2012 - DEC 2014 · 3 years
• Executed $293B in 35+ equity transactions across U.S. and Latin American stock exchanges • Frequently conducted business in Spanish with Latin American clients, including pre-equity issuance due diligence calls held in Spanish • Conducted research and synthesized data to advise management of private and public companies on equity issuance • Founded and co-led internal Deal Review Committee to centralize information across industry teams and enhance the Analyst experience via increased knowledge transfer and client-facing opportunities • Supervised and trained three junior team members • Earned promotion offer to Senior Analyst
Investment Banking Summer Analyst - Equity Capital Markets
JAN 2011 - DEC 2011 · 1 year
• Rotated within the Consumer & Retail, Latin America, and Real Estate Equity Capital Markets groups • Owned development of client meeting materials outlining macroeconomic and equity issuance trends • Presented final pitch to senior leadership of the Equity Capital Markets group analyzing the Brazilian equity markets • Earned offer for full-time Analyst position
JAN 2010 - DEC 2010 · 1 year
Consultant
JAN 2010 - DEC 2010 · 1 year
• Consulted 250+ hours competing in small teams to win business from 6 local Nashville companies: Lexus, Bridgestone, HIMSS Medical Banking Project, Nashville Area Chamber of Commerce, MyWerx, Oasis Center, and Nashville Entrepreneur Center • Won 1st place for the HIMSS and Online Medical Banking project, developing a new revenue-generating strategy and a marketing campaign to gain more advocacy from health insurance carriers • Awarded team MVP for overall leadership in creating a teen-focused viral marketing campaign for MyWerx
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