Leading with Product: Strategies for Overcoming Resistance and Driving Innovation

This is the 3rd in the series of articles about product-led companies. In the first article of this series, we explored how the collaboration between the CPO and CMO and their respective team can unlock new revenue opportunities.

The second piece expanded on the role of product in driving growth, not just through tighter alignment with marketing, but as a foundational business strategy.

That naturally led us to the concept of the product-led company. 

Now, in this third one, we dive into the challenges of making that vision a reality—and how to turn those challenges into opportunities for growth.

A Product-led company places its products at the center of customer acquisition, retention, and expansion. While that may sound intuitive, it introduces a set of real challenges, especially for traditional B2B organizations accustomed to sales-led or marketing-led motions.

Here are some challenges and how to overcome them to make them growth opportunities. 

Lessons learned through my career, I’ve seen how trying to force-fit B2C product-led practices into B2B models can lead to friction and missed expectations.

The shift requires more than just adopting new tools or metrics. It requires a mindset change and deep investment across the product experience with analytics, AI, automation, onboarding, help, in-product marketing, and seamless upsell mechanisms all built into the product.

Resistance from Leadership: Sales, Marketing, and Internal Teams

Challenges

Traditional B2B companies rely on high-touch sales teams for lead generation, conversion, and customer relationship management.

The resistance from sales teams toward self-serve adoption is not just about fearing loss of control or reduced commissions.

The heart of the angst is about the customer relationships sales professionals have carefully cultivated over time. These relationships represent not just revenue, but professional identity and value. 

How to Overcome

Create a Complementary Hybrid Approach

Establish a model where sales teams focus on enterprise accounts and expansion opportunities, while the product drives inbound interest and initial adoption among individuals or small teams.

This approach transforms the sales process from cold outreach to engaging with already-interested users based on product usage signals.

PMs must design the product with a hybrid GTM motion in mind.

This means building a product that can attract and activate users through self-serve, with clear handoff points for sales to step in and grow the account.

Think about how you can surface product usage signals (e.g., active users by area, usage milestones, in-app intent) that sales can act on. PMs should collaborate with operations to define and track metrics like PQLs, conversion rates, and expansion revenue.

This data should be core for every product review and potentially board updates.

This data-driven approach not only helps validate your hybrid strategy but also provides concrete evidence of success, making it easier to align all stakeholders behind the model and convince even the most resistant teams of the value in embracing change. 

Align Strategy with Compensation

Reward sales teams for upgrades and expansions within existing accounts, not just new logo acquisition. Many hybrid strategies fail not because of philosophy, but because of comp plans. PMs should partner with sales leadership to advocate for compensation models.

If sales isn’t incentivized to support product-led motion, they simply can’t prioritize it, no matter how aligned they are in principle.

In nearly every company, my conversation with sales leaders has been some version of this statement.  “We are ready to align with the strategy, our comp model unfortunately does not reflect that.”  

This is an opportunity for all PMs to help reframe this conversation and work closely with Sales and Finance using data and empathy to drive organizational change.

This needs to be part of the PM mindset, every conversation should include the question: “How can I help?” because real alignment starts there.

Maintain Product Excellence

The most critical thing is to ensure your product consistently delivers value without disruption.  For product-led growth to work, all teams need to be bought in, the product needs to be rock-solid. PMs must treat stability and UX not as minor issues, but as core to the value proposition.

If something breaks during a pilot or a key enterprise rollout, trust is lost. As one sales leader once said to me: “Just don’t break it. That’s all we ask.” That mindset needs to be part of every PM’s DNA.

To summarize, Product managers need to move beyond features, user stories, and feature launches.

That means understanding the P&L for your product line, aligning roadmaps with revenue outcomes, and being deeply aware of how costs, pricing, packaging, and adoption affect business growth.

If you want sales to buy into a product-led structure, you need to show up with numbers that prove your product is driving an impact.

Multiple Stakeholders: Product and Pricing Complexity

Challenges

Unlike B2C products with end-users in the driver seat, B2B products face unique challenges with multiple stakeholders, including business leads, IT, security, procurement, and legal teams involved in decision-making.

Companies typically require contracts, procurement approvals, and security compliance before adopting any new software, private or public cloud. B2B pricing models are often customized, contract-based, and require negotiation. Many B2B products require significant implementation and integration time before customers realize their value. 

As a product leader, this environment demands a change in mindset, one that balances enterprise realities with a product-led mindset..

How to Overcome

Optimize Time To Value

Your product shouldn't wait until the contract is signed to deliver value. The product should ensure that new users experience core product value within minutes through intuitive onboarding.

PMS should work closely with the sales team to showcase this during initial sales interactions and use the sales cycle for customers to actively try the product during demonstrations.

Have customers use the product throughout the sales and demo cycle.

Provide design experiences for each of multiple personas (think end-user, IT admin, and decision maker, most likely the CFO) in the room so they can see the value for each of their teams. Build plug-and-play for the most commonly used integrations for your industry, especially the non-negotiable ones.

Personalize Impact Measurement 

Product Managers should provide personalized in-product dashboards that measure impact for each user persona, making process and data metrics specific and using terminology familiar to each user type.

Build knowledge bases, video tutorials, and automated help centers, including the ability to enable customers to customize help content with their internal documentation and compare their process with industry standard processes. When possible, surface success stories and benchmarks from similar companies in the same industry. Customers always ask me, "Who else likes me using it and getting better results?"

Design Clear Value Tiers

Provide transparent pricing and clear security compliance information upfront to eliminate common obstacles that emerge during expansion conversations.

PMs must take ownership of how value is communicated, not just through features, but through pricing and packaging.

This prevents surprises that can strain both customer relationships and internal team dynamics. Develop a hybrid pricing approach combining per-seat, usage-based, and outcome-based models that allows revenue to scale with customer adoption while sharing risk between customer and vendor.

Provide value-based pricing tiers that are easy for finance teams to understand, with low-cost options for SMB customers and premium solutions for larger enterprises familiar with similar models from providers like AWS, Microsoft, or Snowflake.

In Summary, as a PM, you need to make sure the pricing and packaging reflect how customers experience value, how it makes their life easy every day, and to ensure that internal teams (like sales and customer success) are set up to scale that experience effectively.

Managing Customer Success: Lack of Data and Analytics

Challenges

In traditional B2B models, customer success often relies heavily on account managers to handhold customers through setup and adoption.

But a product-led approach flips the model, it encourages customers to self-serve and discover value without high touch. Many B2B companies don’t have the analytics infrastructure in place to support this shift and are reticent to invest in it.

For the product teams, this creates a blind spot.

Without visibility into user behavior, adoption patterns, and drop-off points, product managers are building in the dark. If customers get stuck and the product is not helping them through it, you not only lose the customer, but you also lose the overall trust. And without data, you can't pinpoint which features drive stickiness or where we have usability problems that need to be addressed.

How to Overcome

Make your product self learning

Product Managers need to start designing products that are proactive, not reactive. Think tooltips, contextual nudges, and AI-driven guides that offer help when and where users need it. Layer in knowledge bases, how-to videos, and automated help centers that make support scalable and available 24/7.

The goal is to design an experience where users rarely need to ask for help, because the product anticipates what they need and does it for them. Long-term, aim for adaptive experiences where the product adjusts based on each user's behavior or persona.

That’s where product-led customer success becomes truly scalable.

Investment in the Right Signals 

PMs need to advocate for the right data infrastructure. Focus on meaningful indicators like activation rates, product-qualified leads, and retention metrics that tell you how well your product is performing.

As I would always tell my teams, don't stop at revenue; look at the usage, they normally go hand in hand. When users find value, revenue follows and grows with you. Use that data to constantly experiment.

Test different onboarding flows, pricing tiers, and feature releases. Let the data guide your next move, coupled with the qualitative anecdotes that you hear from your customers

Make CS your best friend (not just sales)

Customer success can’t scale through people alone. PMs should work with CS to define what “good” looks like at each step of the journey, then design the product to get users there faster.

Use Customer Success Managers (CSMs) where they matter most with large, complex enterprise deals that need a high-touch approach. For everyone else, lean on automation, smart onboarding, and in-product guidance to scale efficiently.

Another effective learning experience, pair junior product managers with customer success teams. Have them listen to support calls, dive into churn cases, and shadow onboarding sessions.

It's one of the fastest ways to build real customer empathy and give PMs a front-row seat to what’s working and what’s not. 

In summary, it also sets PMs up for long-term success by grounding product decisions in real user needs. They need to think beyond features and focus on user outcomes, which is what a product-led model demands.

Final Thoughts

Blending Motions, Driving Impact

Shifting to a product-led model in B2B isn’t easy. These are not small changes, but they are necessary ones.

As one of our board members often reminded us (of this JFK quote)  during tough transitions - "We choose to go to the Moon in this decade and do the other things, not because they are easy, but because they are hard.”, this rings true when we have to make fundamental changes.

It means pushing through internal resistance, navigating complex pricing structures, and rethinking onboarding for a more self-serve experience. The prize is lower customer acquisition costs, higher conversion rates driven by self-serve adoption, and stronger expansion revenue through usage-based models.

The key is not to go all-in on product-led at the expense of everything else. It’s about blending the best of both product-led and sales-led approaches. This isn’t about replacing sales, it’s about building a model where product and sales amplify each other.

When you combine seamless onboarding, thoughtful product design, and data-driven decision-making, it's not just transactional, it's building sustainable relationships across the entire customer spectrum, from SMBs to the largest enterprise accounts.

About The Author

Uma Welingkar

Fractional Chief Product Officer

Uma is a strategic product leader with extensive experience in driving innovation, leading global teams, and delivering customer-focused solutions.

Read Uma's bio or book a time with her.