Trust and Alignment in Sales Driven Software Companies How to foster trust and alignment in fast growing b2b software companies

There is a natural tension that exists when building b2b software products.

Sales teams need predictable timelines to close deals and set customer expectations. Engineering teams need time and space to build maintainable products that scale with the business. Revenue teams push for faster delivery so they can meet this quarter's numbers. Product teams push back, concerned about long-term technical debt.

The push and pull is constant, but necessary.

But, is this a problem to be solved or a tension to be managed?

The best companies I’ve worked for don't eliminate this tension—they harness it. They create systems where both sales and engineering understand each other's constraints and work together to make smart tradeoffs.

This post offers practical approaches for both sides. If you're in sales or customer success, you'll find ways to get more reliable commitments from your product team. If you're in engineering or product, you'll discover how to protect what matters while supporting the business.

Two Sides of Customer Value

Both sides of this tension are ultimately fighting for customer value, just in different ways.

For sales and revenue leaders, customer value means delivering on promises right now. Meeting this quarter's commitments. Closing the deal that's on the table. Keeping the customers you already have happy. When dates slip or features get delayed, it's not just an inconvenience—it directly impacts relationships and revenue.

For engineering and product teams, customer value means building something that lasts. Creating a coherent product that can evolve and scale. Avoiding technical debt that will slow down future delivery. When forced to take shortcuts or bolt on one-off customizations, they see the long-term impact on the product's foundation.

Neither perspective is wrong. They're complementary parts of the same goal: creating sustainable customer value over time.

Breaking Down Misconceptions

There's a common belief that engineers don't understand business priorities. That they're too focused on elegant solutions at the expense of practical outcomes. Too concerned with what's right in front of them.

I see it differently. Great engineers are systems thinkers. They're not just thinking about the current feature—they're thinking about how it fits into the entire product. How it might need to scale. How it interacts with existing functionality. How to build it so it won't break when other things change. In other words, they're protecting the product as a business asset. They're thinking about the customer experience six months from now, not just this week's deployment.

Similarly, great sales teams aren't just pushing for features to hit their numbers. They're responding to real customer pain points. They're trying to keep customers from leaving for competitors. They're working to maintain trust in relationships they've spent months or years building.

When engineers push back on timeline commitments, it's rarely stubbornness. It's usually because they see risks or complexity that aren't visible to non-technical team members. When sales pushes for faster delivery, it's rarely impatience. It's usually because they see business opportunities or threats that engineering might not be aware of.

The True Costs of Misalignment

When product tension isn't managed well, both sides pay a price.

For sales teams, missed deadlines damage credibility with customers. Repeated delays erode trust. Customers start to discount timeline commitments, making it harder to close new deals or expand existing relationships.

For engineering teams, constantly shifting priorities and emergency requests create a cycle of technical debt. Features get implemented in ways that solve immediate needs but make future work harder. The codebase becomes more fragmented and harder to maintain with each rushed delivery, leading to more time spent fixing bugs than shipping features.

For the business as a whole, the cost is competitive disadvantage. Companies that can't reliably deliver on promised timelines while maintaining product quality will eventually lose to those that can.

Create a Shared Framework for Decision-Making

The most effective teams I've worked with developed a shared language and framework for navigating this tension. Here's what that looks like in practice:

Different Types of Commitments

Not all deadlines are created equal. Create clarity by distinguishing between:

• Hard commitments: Dates the business absolutely must hit (contractual obligations, regulatory requirements, major customer renewal dates)
• Target dates: Goals the team is aiming for, with some flexibility built in
• Forecasts: Best estimates based on current information, explicitly subject to change

Confidence Levels

Attach confidence levels to timeline estimates:

• “We're 90% confident we can deliver by this date”
• “We're 50% confident we can deliver by this date, and 90% confident by this later date”

This creates more nuanced conversations than simple yes/no commitments.

Clear Prioritization Criteria

Establish a shared criteria for truly urgent requests:

• Revenue impact (with specific thresholds)
• Number of customers affected
• Strategic importance to long-term goals
• Technical feasibility and impact on other work

When sales, engineering, and product all understand how decisions get made, there's a lot less friction when making tradeoffs and deciding what to prioritize.

Practical Steps for Sales Leaders

If you're on the revenue side of this equation, here are concrete steps you can take to improve alignment:

Involve Engineering Earlier

Don’t commit to a date without at least talking to someone on the engineering team. I know what it’s like to have your back up against the wall in a meeting, as the customer tries to pin you down for a date, but nothing puts an engineer on guard like being told they’re on the hook for something they didn’t agree to. A good way to prevent this is to include engineering leads in pre-sales conversations for big deals or complex feature requests. Doing this creates shared ownership of the commitment from the beginning of the process.

Frame Needs as Problems, Not Solutions

Instead of telling the engineering team exactly what to build, focus on the customer problem that need to be solved. "Customer X needs to reduce manual data entry by 50%" gives the technical team more flexibility than "Customer X needs these seven specific form fields that auto-populate."

Build in Buffer Time

When communicating timelines to customers, add buffer beyond what engineering estimates. The more complex the feature, the more buffer you need. A good rule of thumb: add 25-50% to any estimate for significant work.

Learn to Ask Better Questions

Rather than simply asking "when will it be done?", try:

• “What are the biggest unknowns in this work?”
• “What dependencies could impact the timeline?”
• “If we had to deliver something by [date], what subset of this could we realistically complete?”

Be Transparent About Business Impact

Explain the real business consequences of timeline decisions. For example, ”If we miss this date, we risk losing a $200K annual contract" gives engineering context they may not otherwise have and helps them make more informed tradeoffs.

Practical Steps for Product and Engineering Leaders

If you're on the technical side, here's how you can bridge the gap:

Create Transparency Around Prioritization

Make your prioritization process visible and understandable to sales teams. They may not agree with every decision, but understanding the rationale reduces friction.

Communicate Constraints in Business Terms

Instead of explaining technical limitations in engineering jargon, translate them to business impact: "Taking that approach would double our maintenance costs for the next year and slow down our ability to deliver the other features on our roadmap."

Provide Different Confidence Levels

Rather than committing to a single date, offer multiple scenarios with different confidence levels: "We're 50% confident we can deliver by March 1st, 80% confident by March 15th, and 95% confident by April 1st."

Break Work Into Smaller Deliverables

Look for ways to deliver incremental value rather than all-or-nothing releases. "We can deliver the core functionality by January 15th, and these additional capabilities by February 1st" creates more flexibility.

Establish Regular Touch Points With Sales

Don't wait for escalations. Set up regular rhythms to discuss upcoming customer needs, review current commitments, and align on priorities. In my experience, bi-weekly or monthly tend to work best.

Create a process that builds trust and alignment

Ultimately, trust between teams is built through consistent behavior over time. Here are processes that support this:

Joint Problem-Solving

For complex customer requests or timeline challenges, bring sales and engineering together to problem-solve rather than having one side dictate to the other. Look for creative solutions that address both immediate customer needs and long-term product health.

Shared Visibility

Create dashboards or reports that show both sales pipeline and development progress in the same place. This helps both teams see how their work connects.

Commitment Tracking

Keep a simple record of committed dates versus actual delivery dates. Use this not for blame, but for learning: "We consistently underestimate work involving third-party integrations. Let's add more buffer for those going forward."

Blameless Postmortems

Engineering teams run blameless postmortem all the time, why not try applying it to your sales process? When deadlines are missed, analyze why without finger-pointing. Was the estimation process flawed? Did scope change? Were there unexpected technical challenges? Use these insights to improve future commitments.

Celebrate Joint Wins

Recognize and celebrate when the team successfully navigates this tension—delivering on sales commitments while maintaining product quality. This reinforces that both perspectives are valued.

The Alignment Advantage

Companies with a strong alignment between sales, product, and engineering have a significant competitive advantage. They can make and keep customer commitments more reliably. They build more coherent products with less technical debt. They retain both customers and engineers at higher rates.

I've seen this from both sides. As an engineer and product leader, I've felt the pressure of sales commitments that seemed impossible to meet. I've also seen the business impact when engineering couldn't deliver what customers were promised.

Here's what I've learned: the gap isn't about technology or process. It's about trust and communication. When sales and engineering trust each other, they make better decisions together.

The goal isn't about perfect alignment—it's about harnessing productive tension to drive better outcomes for everyone.

Start small. Pick one or two practices from this post to implement. Create a shared vocabulary for different types of commitments. Establish regular cross-team touch points. Build trust through consistent behavior over time.

The most successful companies don't eliminate the tension between sales and engineering—they channel it to create something better than either side could build alone.