Sales Enablement Strategies That Drive Success
From messy pipelines to consistent performance, startup leaders reveal how dedicated sales enablement and sales development hires transformed their sales marketing outcomes—and what pitfalls to avoid.
What Even Is Sales Development, Anyway?
As startups scale, sales teams often find themselves bogged down with tasks that pull them away from selling. Proposals drag, messaging gets sloppy, and onboarding feels like reinventing the wheel. That’s when many founders begin to wonder: is it time to hire for sales enablement or sales development?
We asked a group of founders and marketing leaders across industries whether hiring a dedicated sales enablement or sales development professional made a real difference—and how these roles support broader sales marketing efforts.
Their answers were honest and tactical. Some found that hiring early was premature. Others saw deal cycles shrink and close rates jump when enablement was done right. The key, they said, wasn’t just the hire—it was giving that person real strategic focus and integration with both sales and marketing.
Here’s what worked, what flopped, and how to know when your business is ready.
Sales Enablement Hire Transforms Chaos Into Systems
Hiring for sales enablement isn’t just worthwhile. It becomes essential once your sales team is spending too much time on non-selling tasks. After running an agency for a decade, I’ve seen what happens without someone owning enablement. Sales gets messy. Pitches become inconsistent, proposals take too long, and onboarding new reps becomes painful.
We brought in an enablement hire when the pipeline was healthy but deals weren’t closing fast enough. They didn’t just create resources. They worked closely with the team to figure out what was slowing us down and built simple, useful tools. Quoting frameworks. Objection-handling scripts. A central knowledge base. Things the team actually used.
What worked was keeping it practical. Ramp time improved, sales cycles got shorter, and there were fewer mistakes. What didn’t work was anything too complex. We tried a fancy enablement tool once and no one touched it. Strategy docs looked good on paper but went nowhere.
Enablement works when it solves real problems inside the sales process.
Nirmal Gyanwali, Founder & CMO, WP Creative
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Good Enablement Turns Every Rep Into Your Best
Totally worth it — if your reps are building decks and hunting down case studies instead of selling, you’re burning money. A good sales enablement hire turns chaos into systems: better messaging, slicker assets, tighter handoffs from marketing. The win? Consistency. Every rep sounds like your best one. What works: shared playbooks, battle cards, and call review breakdowns. What flops: bloated content libraries no one uses and training that feels like a TED Talk. If enablement isn’t saving reps time or helping them close faster, it’s just noise.
Justin Belmont, Founder & CEO, Prose
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Connect Marketing With Sales Through Dedicated Enablement
We found out pretty quickly that giving sales teams access to decks and a CRM doesn’t count as enablement. Messaging got inconsistent, and deals were falling through. So we hired someone to focus solely on sales enablement not to just build content, but to actually connect marketing with sales on a daily basis.
One shift that really worked: they started feeding real buyer objections into training sessions and adjusting messaging to how prospects actually decide. That insight alone improved win rates.
What made it work wasn’t just the hire it was giving them a seat at both marketing and sales tables. Without that, it’s just busywork.
What’s failed for us? Creating templates or tools in isolation. If enablement isn’t involved in the sales process, they’re not really enabling anything.
In the end, it’s not about hiring a role. It’s about focus and someone whose focus is on making sales better is always a good investment.
Vikrant Bhalodia, Head of Marketing & People Ops, WeblineIndia
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Sales Enablement ROI Peaks With Double-Digit Teams
Having built multiple companies in the 3PL and eCommerce space, I’ve seen firsthand that dedicated sales enablement can be transformative when implemented correctly, but wasteful when done poorly.
In the early days of my previous ventures, we tried the “everyone does everything” approach to sales. Our pitch decks were inconsistent, our messaging varied between reps, and onboarding new salespeople took months. When we finally hired our first dedicated sales enablement specialist, our conversion rates improved by nearly 30% within a quarter.
The key is timing. For startups or smaller operations, having a specialized sales enablement person is usually premature. Your first 5-10 sales reps should work directly with marketing and product teams. Once you hit double-digit sales headcount or experience rapid growth, that’s when a dedicated resource becomes invaluable.
What works: Creating standardized, battle-tested materials that address specific customer pain points. In the 3PL world, we saw tremendous success with industry-specific playbooks that helped our reps speak the language of different verticals (apparel has very different needs than health supplements). Our best enablement efforts focused on data-driven objection handling and competitor comparisons that sales reps could easily personalize.
Another win: structured onboarding programs with clear 30/60/90 day milestones. New reps who went through our formalized enablement program reached quota 40% faster than those who didn’t.
What fails: Generic materials that don’t reflect real customer conversations. I’ve watched companies waste thousands on glossy sales decks that reps never use because they don’t address actual buyer concerns. Also dangerous is treating enablement as a one-time project rather than an ongoing process requiring constant refinement.
Rather than focusing on fancy tools or automated sequences, the most effective enablement teams I’ve worked with obsessively document customer interactions, refine messaging based on win/loss analysis, and create content that directly addresses friction points in the sales process.
The bottom line: If your sales team is scaling beyond 10 reps or you’re noticing inconsistent messaging and results across the team, a dedicated enablement resource will likely deliver strong ROI. Just ensure they’re deeply embedded with both sales and marketing, constantly gathering feedback from the field rather than creating materials in isolation.
Joe Spisak, CEO, Fulfill.com
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Dedicated Enablement Bridges Critical Marketing-Sales Gap
Hiring a dedicated sales enablement or development role becomes essential as your team grows. From what we’ve seen firsthand, relying on reps to build their own messaging or materials creates friction and slows momentum.
A focused enablement function helps bridge the gap between marketing and sales. It ensures that reps have timely training, relevant content, and a deep understanding of the product.
Things that work well are structured onboarding, objection-handling frameworks, and keeping sales scripts aligned with product updates. What doesn’t work and has failed is treating enablement as a one time setup rather than a continuous process.
Since making it a priority, we’ve seen faster ramp times, better alignment, and stronger overall performance. It’s not just helpful, it’s a key part of scaling a healthy sales operation.
David Batchelor, Founder / President, DialMyCalls
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Sales Enablement Drives 20% Growth, Shorter Cycles
Hiring a dedicated sales enablement or sales development person or team is highly worthwhile when your sales organization is scaling or facing complex buyer journeys. Sales enablement professionals equip reps with the right tools, training, and content to sell more effectively, leading to measurable improvements like 6-20% sales growth and up to a 23% shorter sales cycle.
They add value by:
- Streamlining access to relevant content and insights, letting reps focus on engaging buyers rather than searching for materials.
- Improving lead qualification and prioritization, ensuring sales efforts target high-potential prospects.
- Aligning sales and marketing teams to ensure consistent messaging and better content utilization, which boosts win rates and customer retention.
- Accelerating ramp-up time for new hires and enabling continuous skill development through coaching and training programs.
Successful sales enablement efforts include structured onboarding, ongoing coaching, personalized content delivery, and clear sales process adoption. Failures often stem from lack of planning, unclear roles, or misalignment with business goals, turning enablement into a low-ROI engagement activity.
In summary, investing early in a sales enablement team drives higher productivity, better buyer engagement, and stronger revenue growth-making it a strategic necessity rather than a luxury.
Amir Husen, Content Writer & Associate, ICS Legal
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Marketing Team Builds Credibility and Drives Leads
I didn’t hire a sales team per se, but I specifically hired a marketing team to help me with building an online presence and increasing brand awareness.
And was that worthwhile? Yes.
The efforts that have really paid off and helped me build credibility and trust with my audience, ultimately driving more leads and referrals.
So, to answer the question, is it worthwhile? Absolutely.
Kiel Kellow, Business Owner, Kellow Construction
Need Help With Sales Development? Contact Mandel Marketing.
Sales enablement and sales development aren’t just supporting roles—they’re force multipliers when deployed with intention. Whether you’re optimizing onboarding, tightening your sales marketing alignment, or building battle-tested assets to help reps close faster, the most successful companies treat these hires as strategic partners, not just support staff.
What sets effective enablement and development efforts apart? Relevance. Simplicity. Direct involvement in the sales process. And a relentless focus on solving real pain points—not just checking boxes or building bloated content libraries.
If your team is growing and sales feels inconsistent, now might be the time to invest. Because when sales enablement is done right, it doesn’t just help your reps sell more—it makes the entire go-to-market engine stronger. And coincidentally, Mandel Marketing offers sales dev services.