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20 tips for creating a winning product strategy and roadmap

omar18218

This is an excellent article authored by Mark Strassman. Link at the end of this article.


After over 20 years as an executive leading business lines and product teams at technology companies including Adobe, Macromedia, Autodesk, Blackboard, LogMeIn (now GoTo), and Malwarebytes, I have delivered desktop, mobile, and SaaS technology solutions that have been used by hundreds of millions of users. Across these experiences, I have been a part of businesses and executive teams that have worked well, delivering immense customer and shareholder value; but I have also experienced and witnessed a number of product, process, and execution errors. I learned from these less successful technology experiences and have honed my product leadership processes to avoid them. From these successes and learnings, I built my processes to deliver predictable and repeatable winning products that delight customers and drive business growth.


In this article, I share my 20 essential tips for crafting a winning product strategy and roadmap. These guidelines cover key processes to follow, including alignment with company goals, core competence identification, understanding target markets, and adopting a customer-centric approach. I also emphasis the importance of transparent communication, prioritization, and data-driven decision-making. By following these recommendations, leaders at product-centric companies can enhance their ability to create successful and innovative products that cater to customer needs and drive business growth.

Following are my 20 tips for creating a winning product strategy and roadmap:


1) Align with your Company Goals and Strategy


  • Your product roadmap must be closely aligned with, and roll up to, your organization's overall business goals and strategic objectives. It should clearly articulate how the portfolio will be a part of the company's success, and every product in the portfolio should have a clear line of sight to its contribution to the company’s goals.

  • There can be no product strategy without a clear and coherent company strategy to support it. If the company’s goals and strategy are not clear, then product either needs to demand this from executive leadership, or, at a product-focused company, take it over from leadership and inform the strategy and success metrics.


2) Define your Company’s Core Competence


  • What are the unique set of capabilities, resources, and skills that distinguish your company from competitors and form the foundation of its competitive advantage? What can your company do that competitors cannot or will not easily do? These strengths can include technical expertise, proprietary technologies, specialized knowledge, channels or partnerships, or unique resources.

  • A company's core competencies should provide a sustainable competitive advantage. This means that competitors find it difficult to imitate or replicate these competencies, allowing the company to maintain its market position over time. Your roadmap should continue to widen the moat of your core competency, and increate your competitive differentiation and separation.

  • "Core versus context" is a concept that helps companies prioritize their resources and efforts when developing products or services. It encourages them to focus on their core competencies and essential activities while outsourcing or minimizing efforts in areas that are not directly related to their primary business goals.

  • Core: These are the activities and competencies that directly contribute to a company's unique value proposition and competitive advantage. Companies should invest heavily in their core areas to excel and differentiate themselves in the market.

  • Context: These are the peripheral or non-core activities that are necessary for business operations but do not directly differentiate the company or provide a competitive advantage. Context activities can include administrative tasks, IT infrastructure, and various support functions.

  • By understanding the core versus context concept, companies can make informed decisions about where to allocate their resources. They can prioritize investments in their core activities, which drive innovation and customer value, while finding ways to efficiently manage, outsource, or partner for context activities to reduce costs and free up resources for strategic growth initiatives.


3) Identify your Target Market


  • If you are something for everyone, you are everything for no one. Instead, be everything to someone.

  • Deliberately choose market segments, and their buyers and users, and build solutions and channels that meet stated and unstated market needs. Customer segments can be vertical markets, size of company, geographies, sets of customers with a unique and shared set of workflows, customers who buy in a unique way, or any set of common characteristics that allow you to uniquely understand, solve for, and deliver a solution set to that segment.

  • Empathize with your target customer group to understand the market needs more than individual customers articulate their individual wants. Learn what they are trying to do, and what is not working well about their current tools and processes. Get out of leapfrogs, and truly differentiate — identify core competencies, innovate based on customer understanding, and double down where you are winning and on what competitors cannot or will not do for this market segment.


4) Understand your customers’ Jobs To Be Done


  • The Jobs To Be Done (JTBD) methodology is a customer-centric approach to product and service innovation. It centers on understanding the fundamental "jobs" or tasks that customers are trying to accomplish in their lives, rather than merely focusing on product features or demographics. JTBD emphasizes uncovering the underlying motivations and context behind consumer choices. By purchasing your solution, they are hiring you for a job they are trying to get done.

  • By identifying these jobs, companies can design solutions that align with customers' goals, leading to more effective and customer-driven products. This methodology encourages a shift from traditional market segmentation to a deeper understanding of customer needs and helps organizations create products that not only solve problems but also resonate with consumers on a fundamental level, ultimately fostering long-lasting customer satisfaction and loyalty.


5) Drive customer insights through Design


  • Design plays a pivotal and differentiating role in a technology company's success. Design ensures products truly meet the needs and goals of their users.

  • Design research informs decision-making by gathering user insights. It is critical as it uncovers user workflows, preferences, and pain points, ensuring that products are user-centric, effective, and market-competitive.

  • Design thinking is a problem-solving approach that emphasizes empathy, creativity, and user-centered solutions. It involves understanding user needs, brainstorming ideas, prototyping, and iterating to develop innovative and effective solutions. This iterative process encourages collaboration and a deep understanding of user experiences, driving innovation and product development.

  • Design has the luxury of being charged with focusing solely on the user – driving insight, understating, and ultimately designing the user experience that addresses them. Product management, on the other hand, has to take a much borader view of the business case, the market environment, market relevance, differentiation, coordination with go-to-market, and more.

  • Both functions are crucial, with design ensuring user insight and delivering delightful experiences, and product management guiding products’ strategic direction and commercial success.


6) Understand your Competition


  • Conduct competitive analysis to gain a comprehensive understanding of the market landscape. Research competitors' offerings, pricing strategies, strengths, and weaknesses. This analysis helps to identify market gaps, inform product positioning, and highlight opportunities for innovation.

  • Don’t just look at competitor’s Web sites. Install and test their products. Benchmark their performance. Find out where they fail. Listen to customers of their products, and your customers who left competition to use your products. Build your positioning and roadmap to widen the moat of where you are better than them.


7) Involve Internal Stakeholders


  • Although product is trained to focus on the needs of the market, the buyer, and the user, it is crucial to both listen to other stakeholders, and make sure they feel heard.

  • Set up regular sessions with sales, marketing, support, and executives, and make sure their product ideas are documented and considered. When the roadmap is published, make it clear why their features were (or were not) included, based on their impact to the thematic success metrics.


8) Proclaim your North Star


  • A North Star is a high-level, aspirational statement that outlines the long-term goals and direction of a technology and portfolio vision. It provides a clear, inspiring picture of what the product should become, aligning the team's efforts and guiding decision-making. It's crucial for a technology product company because it serves as its desired end-state, fostering alignment, motivation, and a shared understanding among teams. It helps prioritize features, stay customer-centric, and adapt to market changes, ultimately driving innovation, growth, and sustainable success.

  • With your understanding of a market and it’s needs, what is your ultimate solution set in 2+ years? If you are successful in your product vision, what does your portfolio look like? Be specific. Spell it out. Make mock-ups and sketches. Test it with customers. Your short-term roadmap should build to this long-term vision. If you are building features without this long-term state in mind, you may be building things that slow down your pace, or distract you, from where you want to be headed.


9) Set your Product Positioning


  • Once you have aligned on a strategy that uniquely solves the jobs to be done for given market segment, and is anchored in your company’s core competency and competitive advantages, be specific and deliberate about your product positioning.

  • Positioning is not something that marketing does after you build your product. You should build your positioning statement before you spend engineering resources to build anything.

  • The typical statement follows this still-relevant, time-tested template:[Product Name] is a [product category] that [unique value proposition]. Unlike [competitor products], it [points of differentiation]. Our product is designed for [target customer segment] who [customer needs/goals].

  • A product position statement is important as it defines and distills a product's unique value, target audience, and competitive edge, guiding product development, marketing, and sales efforts for effective market positioning.


10) Be clear and deliberate about what features are Table Stakes or Good Enough


  • A "table stakes" or "good enough" feature on a product roadmap refers to a functionality or capability that is considered essential or baseline for a product to be competitive or meet the minimum expectations of its target market.

  • These features are not typically innovative or differentiating but are necessary to satisfy basic user requirements and remain on par with competitors. They serve as a foundation upon which more advanced or unique features can be built to differentiate the product further. Prioritizing table stakes features ensures that the product is viable in its market; however, you must be careful not to spend too much time or resources on these non-differentiating, “check-box” features.

  • Focus innovation and differentiation on your core differentiators, while making sure you spend only the minimum resources to meet the requirements of these “good enough” features.


11) Be explicit about the Role of Each Product in your Portfolio


  • Much like customers buy your products for their jobs to be done, each product has a job to be done in your holistic solution portfolio.

  • If one of your main products is a mature product in a mature market, be clear about what you want it to do. – Is it a cash cow that you should optimize for profitability, or do you need to invest to transform it or defend its market position? Set KPI’s that make its role clear.

  • Do you have add-on products, or tiered bundles or modules to increase upsell and Net Revenue Retention (NRR)? Be deliberate about the success metrics based on the intended product goals.

  • If you have free or trial products that serve to “land” users, set expectations that their success is not direct bookings, but leads generated and contribution to long-term customer value, and its ROI should be judged with a Lifetime Value to Customer Acquisition Cost (LTV to CAC) ratio, or upsell metric.

  • Every product portfolio should include investing in innovation to drive future growth. Establish and socialize a portfolio innovation funnel for your company. A product portfolio innovation funnel is a strategic framework to manage the investment into and selection of new product ideas. It involves stages such as idea generation, idea testing, prototyping, development, testing, and launch. To manage it effectively, a company should generate a lot of innovative ideas, but minimize the investment in individual projects until they pass success gates. Many ideas will drop out of the funnel, and successful ones will pass further down the funnel, receiving more investment as they graduate through progressive success gates.


12) Set Roadmap Themes and Big Rock Features with clear success KPI’s


  • Your product roadmap should be based on a small number of themes and incorporate clear KPIs (Key Performance Indicators) and success metrics per theme.

  • Themes provide a strategic focus, allowing teams to align efforts towards overarching goals, fostering cohesion, and preventing feature bloat.

  • Clear KPIs and success metrics for each theme serve as objective yardsticks to gauge progress and ROI. They enable data-driven decision-making, helping teams identify what features make the most impact to each theme, what’s working, and what needs adjustment.

  • This approach enhances accountability, transparency, and customer-centricity by ensuring that product development efforts directly correlate with thematic business objectives and customer needs, ultimately leading to more effective and successful product outcomes.

  • The big rock, small rock, pebble, sand analogy in product roadmapping represents prioritization. Given a fixed size container, you put in the big rocks first, then then small rocks, then the pebbles, then the sand. – If you were to put in the sand, then the pebbles, then the small rocks, the big rocks would not fit into the container.

  • Big rocks are critical, high-impact tasks. Small rocks are important but less urgent. Pebbles are less significant, and sand represents minor, often time-consuming details. Prioritize big rocks first, ensuring essential work gets done before focusing on less critical elements.

  • Big rock features, also referred to as "rockstar features" or "killer features," are the standout and game-changing functionalities within a product or service. They are the key elements that significantly differentiate a product in the market, driving user engagement and competitive advantage. These features are not only robust but also align closely with user needs and desires, offering exceptional value.

  • Companies strategically prioritize and invest in big rock features to create a compelling user experience, boost customer satisfaction, and propel their products ahead of competitors, ensuring their products stand out in a crowded marketplace and become a driving force behind the product's success.

  • Fill your roadmap first with big rock features that deliver on the KPI’s, or success metrics, of each theme. Then, if there are available resources, add in small rocks, pebbles, and sand until the roadmap is full, and development resources are fully utilized.


13) Make Transparent Trade-Off Decisions


  • Never say “yes” or “no” to any items on a roadmap. Every choice is a deliberate trade off. You need to make these choices transparently, and with a clear and published rubric based on impact to the business.

  • Prioritize the items on your roadmap based on their impact and effort. Use techniques like the Eisenhower Matrix, the Kano Model, or a scoring system to help determine which features or projects to tackle first. Consider dependencies between items and create a logical sequencing to ensure efficient development. Prioritize “low-hanging fruit.” – Features that bring a high impact with minimal effort.

  • If new ideas are generated for the roadmap (as they always are), whether from customers, engineering, executives, or in response to competition, evaluate these new ideas based on their ability to meet or exceed the success metrics of each given theme to which the feature is assigned. Make this trade-off process, and the math behind it, deliberate and transparent.


14) Choose a System of Record and make it available to everyone in the company


  • Companies should use roadmap tools like Aha!, Productboard, Atlassian Portfolio, or shared spreadsheets or databases to effectively plan, communicate, and execute their product strategies. These tools facilitate alignment among teams, prioritize features, track progress, and provide visibility into the product development process, ultimately leading to improved product delivery and customer satisfaction.

  • Put all feature requests and product ideas – including thematic area, impact to KPI’s , engineering level of effort, and committed or intended delivery dates – in your system of record, and make that live roadmap available to everyone in the company.

  • If a date slips, or if you defer one feature in favor of a new, higher-impact one, publish these changes in a regular digest, so that all functions stay aligned.


15) Communicate Roadmap, transparently and clearly


  • Effective communication is crucial for gaining buy-in from stakeholders and keeping the team aligned. Share your roadmap with all relevant parties, including developers, designers, marketers, and executives.

  • Simplify the full roadmap to a single page digest, with a row for each theme (along with its success metric), and a column for each of the upcoming 4-6 quarters, with the committed and intended “big rock” features that are being delivered per theme, per quarter.

  • When you make roadmap changes, be transparent about the timeline, trade-offs, priorities, and any potential risks or uncertainties.

  • Set up regular, cross-functional product updates to share roadmap changes, reasons for trade-offs, and demos of early designs and pre-releases.


16) Track your business on a simple, One-Page Dashboard


  • Build, maintain, and update a one-page view of your business, organized by theme, with stated and agreed upon goals and KPI’s per theme, and progress towards each goal.

  • Ideally, this is a live dashboard with constantly updated data. If not, update it at least weekly. Start every executive team meeting reviewing this dashboard, highlighting and spending the most time on where KPI’s are tracking to miss the goal (highlighted in red.)

  • For areas that are underperforming, assign leaders to own, diagnose, and come back with clear solutions, or, if the committed tactics that were expected to drive the success metrics are failing to do so, be realistic about whether to double down on them, or to move to different tactics that have a better chance of success.


17) Establish a User Feedback Loop


  • Establish a feedback loop with users to gather insights for continuous improvement. This can include in-product telemetry, user testing, surveys, and customer support channels.

  • Use this instrument to not just listen to and incorporate the feedback of users to iterate your roadmap, but make this a closed-loop communications, responding to users, letting them know you are listening, and setting specific expectations about what you are doing with their feedback.

  • Consider using an “experience management” product such as Medallia, Qualtrics. Such platforms’ robust customer experience management capabilities allow businesses to gain deeper customer engagement and satisfaction analysis.


18) Double Down on What’s Working, and divest of what is not


  • Gather and assess the data about what is truly working – where you are growing, what customers love the most, segments where you are most winning, and where you are beating competition, then refine your strategy to double down on what’s working.

  • While you do need to give new growth areas time to mature, you also need to be realistic about not escalating commitment to something that’s simply not working, and instead divert those resources to those strategies that are.

  • Set up clear profitability timelines for new projects to align ROI expectations, and establish “crawl… walk… run…” milestones to track progress to your goals. If you are not meeting progress expectations, be honest about whether to double down or to pull back.


19) Run Win-Loss Analyses


  • Don’t just rely on sales win/loss reasons in your CRM, but run cross-functional win/loss analyses with both won customers and lost prospects.

  • Running win/loss analyses is crucial for a company to gain valuable, real-world insights into its competitive position, product strengths, weaknesses, and customer preferences. It helps refine strategies, improve products, and adapt to market dynamics, ultimately enhancing decision-making and increasing the chances of long-term success.

  • If you have not already separated your customers into groups of cohorts, with similar buying, retention and expansion characteristics, the win/loss analyses are a great place to start.

  • Hiring a third-party consultant to conduct these analyses can be especially valuable, proving both an unbiased cross-functional view, and helping to solicit more honest and direct feedback from customers and lost prospects.


20) Embrace, encourage, and create a culture of Healthy Conflict


  • Embracing and mining for healthy conflict is crucial because it fosters diverse perspectives, encourages critical thinking, and sparks innovation. It allows teams to challenge assumptions, identify weaknesses in strategies, and arrive at more well-rounded decisions. Ultimately, this leads to improved problem-solving, stronger teamwork, commitment, and accountability.

  • Whether in decision-making, in post-mortems after shipping a product, in choosing what tactics will best meet the target KPI’s and goals, or in any collaboration, healthy conflict is crucial for continuous improvement.

  • End every meeting asking if any attendees disagree with or take issue with the decisions from that meeting. Do not tolerate “meetings after the meeting” where attendees leave a meeting then share dissent with only one or two of the attendees. Encourage and reward dissent and discussion in the room, so that it can be recognized, discussed, and addressed.

  • Allowing everyone to have a voice, identify areas for enhancement, and learn from mistakes, will not only maintain a culture of transparency and accountability, but will foster innovation and deliver better products to customers.


These 20 tips for creating a winning product strategy and roadmap offer a guide for product leaders and teams seeking to achieve success in today's competitive technology landscape. Drawing from my experience, these insights emphasize the importance of alignment with company goals, understanding core competencies, and identifying target markets. Moreover, they highlight the significance of customer-centric approaches, transparent communication, and data-driven decision-making.


The emphasis on prioritization, focusing on core differentiators, and making transparent trade-off decisions underscores the need for strategic thinking and efficient resource allocation. Additionally, the inclusion of tracking to a dashboard and win-loss analyses emphasizes the importance of continuous learning and adaptation.


Ultimately, these tips provide a roadmap of their own for building and implementing a best-in-class product practice that not only delights customers but also drives sustainable business growth. By following these guidelines, product leaders can navigate the complex challenges of the tech industry and increase their chances of creating products that stand out and succeed in the market.


 
 
 

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