The quarter is only halfway through, and your team is already scrambling. Pipeline feels lighter than forecasted. A few top reps are carrying the weight. And a handful of “hot” opportunities are quietly slipping into next quarter.
This is the moment when sales leadership matters most. Sales leaders are facing macro headwinds, evolving customer expectations, and shrinking budgets — all while trying to align their teams, maximize pipeline efficiency, and focus on building a scalable sales motion that drives long-term growth.. That’s why we brought together sales leaders from across the Madrona portfolio for our first Sales AMA, where we dug into the systems, mindsets, and signals that separate reactive sales cultures from high-functioning revenue machines.
If you’re a sales leader trying to build something predictable, scalable, and truly cross-functional — not just scrape across the quota line — these five focus areas will help you move beyond the fire drill — and toward building a scalable sales motion that can stand up to changing conditions.
Start with Foundations: Set Goals, Design Programs, Measure What Matters
Whether you use OKRs, V2MOM, or OSMs, the principle is the same: Set 3-5 clear goals that matter most to your business this year. These goals should be tied to your revenue target, your product motion, and your company stage.
From there, work with your first-line leaders to prioritize a few programs that could meaningfully move the needle. If your goal is to improve rep productivity, maybe that means launching new enablement tracks or testing vertical-specific messaging. If it’s pipeline growth, perhaps it’s Pipeline Tuesdays and doubling down on outbound motion.
Critically, define the leading indicators that will signal early if a program is working. These should be co-created with your managers so they understand how daily activity ladders up to company goals. Are we seeing more meetings booked? Are deals moving through early-stage funnel milestones? Are conversion rates improving? Monitor these metrics at least twice a month with the team.
This structure — 3-5 goals, focused programs, leading indicators — creates clarity, accountability, and a shared language across sales, marketing, product, and finance. It also gives first-line leaders a seat at the table and helps connect strategy to execution.
Ask: What Would Have to Be True?
Once your foundation is in place, step back and ask the question most sales teams never do: What would have to be true to grow faster?
This shift in mindset can be a big unlock. Instead of building quota from the bottom up (“how many reps do we have, what’s the ramp time, what can they book?”), the team started setting aspirational goals and working backwards. Could we double next year? Triple?
That’s when conversations change: Do we need more recruiters to hire reps faster? More BDRs to fill the top of funnel? Better tools to speed up onboarding? Or a new lead-gen motion entirely?
When you plan from possibility, not just probability, you force your organization to consider constraints — and how to break them.
This is not fantasy. It’s investment-oriented planning. And it puts sales in a position of proactive growth leadership, rather than reactive goal defense.
Turn Disqualified Pipeline into Future Revenue
Disqualified pipeline isn’t a dead end — it’s a roadmap. If someone said no today, it often just means “not yet.” The challenge is: What happens to that contact after the disqualification?
You should treat disqualified opportunities as future pipeline. Partner with marketing and SDRs to create nurture tracks. Have your reps check in quarterly with value-add insights: a new product launch, a relevant article, a compliance update that might change their timeline.
Just as important: Know when to disqualify in the first place. One of the most useful qualification filters: Do they have budget or just intellectual curiosity? Curious buyers aren’t necessarily urgent buyers. Help your reps identify which is which, and you’ll save hundreds of hours and keep your pipeline honest.
If Reps Aren’t Hitting Quota, Ask: What Did We Get Wrong?
When your team misses, start by looking in the mirror. If you hired strong reps with a track record of success and they’re underperforming now, something upstream is likely broken.
Start with the basics. Are reps armed with the right messaging — value-based, pain-oriented, competitive-aware, and grounded in the reality of your customers’ day-to-day? Are you training reps on how to position your product in the context of competitor contracts, pain points, or objections?
Are you asking them to break into new markets without support? You might consider reshuffling quotas during exploratory GTM shifts to encourage teams to test and learn. Use the data to reset a fair baseline and build back from there.
When things aren’t working, the answer isn’t always “work harder.” It’s usually “work smarter, together.”
New Tech, Same Playbook: AI at the Top of the Funnel
The AI boom is shifting how companies prospect — but the playbook for evaluating tools hasn’t changed. Several leaders that joined our AMA shared early experiments with Clay, Common Room, 11x, and Reply.io. The results? Too soon to call, but promising.
What matters isn’t the tech alone, but how you use it to identify and act on pain. The future of AI in sales isn’t just lead gen — it’s contextual qualification, outreach personalization, and objection handling. AI won’t replace your team, but it can supercharge them. Most importantly, the AI space is evolving for GTM teams. Keep a close eye in the next 12-18 months for technology that creates a whole new process and future for your team.
If you’re testing these tools, start with these questions: What process are you trying to improve? What KPIs will prove it worked? And most importantly, how will you feed those insights back into your GTM system? In addition, some of the legacy platforms (Gong, Outreach, Salesloft, etc.) have created AI capabilities. Before you rip and replace, make sure you understand what technology they have added and if this solves the gaps you are experiencing vs. training the team on a series of new AI point solutions while you wait for the AI space to mature for GTM teams.
Looking Forward
Great sales leadership today requires more than forecasting accuracy or coaching excellence. The best leaders are strategic operators: setting goals, designing programs, measuring outcomes, and asking bold questions about what’s possible. Sales is truly both science and art. The science comes from data, metrics, process, and experimentation. The art comes from how you align your team, inspire your leaders, and push your company to think bigger.
It’s not just about how you hit your number. It’s about building a scalable sales motion — a machine that hits the next one faster, smarter, and together.
This guide came from our June portfolio company Sales Leader sessions. Keep an eye out for takeaways from the first-ever Finance Leader session we also launched in June.