United States

Generalist Product Management

UX Design

Product Design

Customer Experience (CX)

Growth Product Management

Data Product Management

Platform Product Management

Group Product Management

Business Development

Product Marketing

Rosaalie Shah

Former Head of Product

Communication

Collaboration

Problem-solving

Time management

Critical-thinking

Empathy

Team player

Organisation skills

Presentation skills

Conflict resolution

Stakeholder management

Leadership

Analytical skills

Public Speaking

Negotiation

AI/ML

Email marketing

Market research

Marketing strategy

Monetisation

Partnership

Product analytics

Product roadmap

Product strategy

Prototyping

Qualitative research

Quantitative research

Relationship management

User research

Trello

ChatGPT

Figma

Miro

Confluence

Branding

Introduce yourself, define mentoring expectations and goals. Learn and grow together.

General mentorship

Making remote and globally distributed teams work for you and your needs.

Working remotely

Learn essential burnout prevention techniques and replenish physical and emotional energy.

Managing burnout

Talk to people who have learned to manage their imposter syndrome.

Dealing with imposter syndrome

Navigating micro-aggression, getting paid what you are worth and finding a community.

Being a woman in tech

Understanding factors that lead to a motivated team - recognition, communication and more.

Keeping team members motivated

Understand the process of training, motivating and directing your team members.

Managing people

How to create a positive workplace culture that drives collaboration and productivity?

Fostering a good team culture

Steps to building and maintaining a strong, cohesive and effective team.

Building an effective team

Learn the tips to successfully manage a team in a remote environment.

Managing a remote team

How to determine what is a good balance of skill sets for your organization's needs

Building balanced teams

Strategies for maximizing your design internship or co-op program.

Getting the most out of my internship

Tips for transitioning into a new role or company.

Changing roles

How to successfully prepare and position yourself for a job promotion?

How to get promoted

How to ask for a promotion and negotiate for salary raise?

Negotiating a job offer

How to think about design career paths and what progression looks like for designers?

Design career path

Learn the career path and progression for product managers.

Product management career path

Get actionable feedback on your resume or portfolio.

Resume and portfolio review

Practice HR, technical and behavioural interviews with mentors.

Practice mock interviews

Talk to people who've broken into the tech industry and learn their stories.

Breaking into tech

How to set up the team for success by defining and measuring team's performance.

Choosing metrics and team goals

How to define and execute a successful launch and managing stakeholders expectations. (eg. MVP)

Launching new products or features

Manage team expectations and get the most out of your meetings.

Running effective meetings

Identify and define potential product problems and generating possible solutions.

Identifying problems vs solutions

Learn how to properly present your work and share ideas and opinions.

Presenting your work with impact

How to work with team members with different skill sets but towards a common goal?

Working cross-functionally

Navigating the working relationship with PM's and engineers as a designer.

Working with product and engineering

How to set up product analytics and metrics to track success?

Leveraging Product Analytics

How to create personas, and leverage them in design.

Creating and leveraging user personas

Ways to provide constructive feedback to team members.

Giving effective feedback

How to define an ambitious product vision and how to best communicate it to stakeholders?

Creating a product vision

What is a successful user onboarding flow and how to achieve it?

Onboarding new users

How to conduct interviews, what to ask, and how to analyze your results? (eg. user interview)

Conducting effective customer interviews

Sidebar is a private, highly vetted leadership program that accelerates your career. We have the people, the process, and the technology to drive your impact and growth.

Part of the executive leadership team enabling organizations and governments globally to achieve success in upskilling, reskilling, hiring and retaining their employees. Helped governments and non-profits globally close the skills gap and empower their citizens to transform their lives through workforce development initiatives.

• Scaled Enterprise SaaS products, foundation of the $200M+ Enterprise business, achieving 21% y/y growth and 98% retention rate. Increased NPS by 5% - 9%, with government clients at 81 NPS.

• Designed internationalization strategy to minimize business model risks and expand global access to education. Increased pipelines by 30%. International market expansion generated $##M in revenue in 6 months.

• Championed first-to-market Gen AI interactive learning assistant, boosting B2B/B2G user retention rates and contributing to $##M in Enterprise revenue saved (reduced churn).

• Overhauled B2B user experience, increasing enrollment rate by 33% through AI-driven learning pathways, reducing user drop-off and improving ROI. 

• Revamped Coursera’s AI Skill knowledge graph, productizing existing data while addressing scalability issues. New skills-first features increased enrollment rates by 25%, lesson completion rates by 75%, and time spent on platform by 50%.

• Optimized Enterprise lead generation sites and B2B self-serve product, driving 12% increase in new sales and 15% retention growth through improved lead qualification, pricing, and positioning strategies. Highest margin product at Coursera.

• Refocused OKRs to prioritize data-driven renewal metrics versus individual feature adoption, eliminating previous MAU cannibalization.

• Product executive skilled in driving revenue through collaboration with GTM teams, leveraging product launches and executive presence at marketing and customer events. 

• Successfully led multiple partnerships and integrations within the HCM and LMS ecosystem, including expansion of product partnerships team.

Promoted to product lead for the acquisition of a marketing automation solution, subsequently becoming Head of Product for acquired company.

• Launched strategic shift from a $100M single product offering to a product suite approach, enhancing market responsiveness, product focus, and revenue opportunities.

• Developed a vision, product portfolio roadmap, and global GTM strategy to increase customer base (revenue) and expand multi-product offering (market value).

• Initiated and led a strategic move to elevate SMB product line to target the mid-market sector for enhanced cross-selling and added value for multi-product customers. Secured board approval for $#M in funding and expanded multi-product customer base from 6% to 51% within two years. Implemented product-led growth strategies to reduce sales cycle, improve user onboarding, retire features to create focus, and collect user feedback

• Launched AI-powered lead segmentation, prioritization, and nurture builder enabling up to 10x faster campaign creation, 25% higher CTR and 50% reduced workload by customers.  Features included dynamic micro-segmentation for campaigns and onboarding, capability leveraging machine learning to uncover hidden opportunities and new markets, and improved forecasting predictability.

• Elevated Gartner’s Magic Quadrant standings by 5% to 7% across critical capabilities within one year.

• Successfully integrated teams, product, and processes post-acquisition while retaining all targeted employees.

Promoted to advance Sugar’s vision shift to a CX Platform. Built and led cross-functional teams to enhance user experience across the entire product: sales, marketing, service, business process management, and integrations.

• Key leader to drive strategic pivot to a cloud-first model. I redesigned the release cycle from 6-18 months (variable) to quarterly and annual releases for cloud and on-premise, respectively. This accelerated product innovation, elevated company valuation, and led to a successful private equity acquisition in 2018.

• Led the development of user-centric product experiences and enterprise features that increased user engagement and customer retention, achieving a 400% rise in new sales and upsells to the enterprise product over three years, representing 70% of company's annual recurring revenue (ARR).

• Designed GDPR compliance feature set. Received industry recognition as the first Enterprise CRM platform to successfully execute in-product data privacy management controls.

• Redesigned product management frameworks to focus on market trends, user analytics, customer needs, and revenue. Developed a data-driven roadmapping approach and product review process to gain visibility and expedite decisions.

• Designed an internal communication strategy to support the entire customer lifecycle from product launch, go-to-market (GTM) activities, internal and external sales channel engagement, and ISV channel operations, through significantly bolstering customer success and support operations, improving overall sales knowledge, customer support and customer success.

• Hired, empowered, and promoted a team of talented and high performing Product Managers. Managed out underperforming PMs, as necessary.

Advisor for startups focused on language learning, education technology, customer experience management, e-commerce, marketplace models, and product management tools.

Personalized 1:1 product management coaching

Established product-market fit (PMF) for enterprise offering, resulting in 81% y/y growth in ARR (annual recurring revenue) for the company’s enterprise business line within two quarters of launch. Managed two product managers.

• Drove enterprise product definition, global GTM strategy, including product pricing, positioning, messaging and value proposition, leveraged in both internal and external communications - improving upsell by 28% 
 
• Integrated acquired product to create PMF for enterprise customers. Defined product and GTM strategy (with PMM & Sales) which resulted in 40% growth in enterprise product upsells within first quarter, compared to typical ~1% conversion per quarter in past years. 

• Drove product definition and requirements for a Fortune 5 client, successfully negotiating features, product development timelines and integration strategies in order to recognize revenue earlier.

Recruited to own and grow Magento Connect, the largest global ecommerce app marketplace.  Charged with growing applications and integration solutions globally.  Championed the need for growth while maintaining integrity of the three-sided marketplace. Delivered comprehensive product vision, roadmap, GTM strategy and a developer community. Dotted line management for 2 PMs abroad. 

• Transformed “Challenged” marketplace into a “Major benefit” for the company - Forrester

• Led growth initiatives doubling number of apps and developers contributing within 2 years, including promoting strategic integrations between Ebay, PayPal and BillSafe.  Cross-business unit promotion

• Lead first build vs. buy decision within the organization – global roadshow and coaching on making product decisions, as well as, showcasing successful OKRs

• Increased engagement and conversion through roadmap feature prioritization using market research, large dataset analysis, NPS, partner input and various user feedback channels.

• Developed relationships and managed expectations for technology partner integrations.


Led cross-functional global teams on multi-year project to improve Magento's platform software by simplifying complex user flows, updating technology stack and optimizing performance. 

• Streamlined user experience flows by 80%.

• Consistent on-time delivery while working with distributed groups of product managers, engineers, ux and product designers, legal, business development and marketing teams.

Promoted to lead cross-functional corporate strategy team to explore multiple initiatives to enhance customer engagement and improve company’s position in the local search space.

• Lead an organizational initiative to disrupt and pivot from a pure advertising business model to a comprehensive SMB business automation and management solution - which it is today.

• Lead strategic partnerships with content vendors to drive advertiser and consumer engagement. Managed content and API integrations across desktop, mobile and tablets – negotiated deal terms to create additional revenue streams. 

• Designed consumer advertising products across desktop, app and mobile web. Leveraged site, client and revenue metrics to build business cases and champion vision to senior staff.

• Primary owner of the consumer product strategy, roadmap, and go-to-market plan for top revenue-generating categories and consumer engagement features, including user registration, user favorites, sharing and social integrations to improve consumer engagement and retention. 

• Created business requirements, product roadmaps, personas, wireframes and requirements docs. Collaborated with business development, editorial, design and agile engineering teams.

Hired to reverse eroding revenues for acquired company while transforming business model from print to digital.

• Successfully reversed revenue loss, contributing to first year revenue growth of 21%.

• Created an entirely new, high performance user experience by implementing a set of vertical consumer sites from ideation through launch, market positioning and sales enablement, improving lead quality by 50%.

• Product lead for site user experience including: information architecture, editorial content, original consumer tools, consumer search, and advertiser display logic.

• Identified and analyzed key performance indicators to drive product improvements – delivered
milestones ahead of schedule ensuring companywide year-end bonuses.

• Introduced and implemented a new Content Management System, designed comprehensive information architecture, guiding the entire process from content acquisition, editorial through publishing and maintenance.  This led to improved site SEO traffic by over 30%.

Member of the executive team defining company’s business plan, vision, mission, branding, positioning, monetization. Defined and launched 0-to-1 product.

Product & Marketing Director					 		
• Responsible for end-to-end of launch company's ecommerce site - expedited launch by 2 months

• Designed product development process enabling real-time communication between remote resources on a zero budget - increased productivity by 30%.

• Revised design of projected highest selling product - reduced fixed costs by 25%

• Designed and implemented new product production process for forecasted scalability issues of adding 10K+ skus weekly

• Increased sales, global brand awareness and recognition through marketing strategy including SEO, SEM, partnership marketing, and cross-promotional online/offline campaigns.

• Managed hires and dismissals of staff
	

Business Development				 			
• Conceptualized and championed higher margin B2B market opportunity. Company pivoted to B2B.

• Identified clients, cultivated strategic partnerships, and negotiated deals - 60% of B2C sales and largest B2B deals

Optimized ticket sales through market research & analyzing marketing campaigns to identify target demographic for radio promotions, ticket pricing and on-sale dates.

Secured proper brand recognition for clients by managing worldwide delivery of offline & online marketing collateral.

Managed client and vendor relationships.

Managed 300+ visual media projects for promotional and commercial worldwide distribution across web, mobile, DVD, television and radio. 

Led development cycle including creative definition of content with clients and internal departments, budget management, contract negotiation, vendor relationships, production, post-production and delivery.

Improved time to market by identifying bottleneck and developing a legal document & records system to streamline processing.

Coordinated product rollouts by managing and communicating weekly status reports company-wide.

Scheduled and maintained artist itineraries on international press junkets and promotional tours, including the Pearl Jam sixteen-country/five day press schedule.  

Analyzed sales reports to improve international/domestic marketing strategy.

Rosaalie Shah🇺🇸

About Rosaalie Shah

Expertise