I just returned from a weekend getaway to Waiheke Island with three colleagues I've worked with for over 15 years in the telecommunications industry.
Reflecting on our journey together was fascinating—what started as peer-to-peer relationships evolved into client-account manager relationship, then back to peers, and once again to professional collaborations.
It’s a testament to how enduring and dynamic professional relationships can be, don’t you think?
Surprisingly, despite our long history together, this was the first time we took a "no work, just rest and relax" trip. We spent time reflecting on the challenges of the past year and sharing our aspirations for a brighter 2025.
We also spoke about the current realities of enterprise and B2B sales, acknowledging just how tough things have been lately. The conversation quickly turned to the importance of resilience, strategic patience, and staying grounded during these difficult times.
In today’s newsletter, I’d like to share insights, lessons, and client successes, hoping they’ll inspire and support you as we navigate these challenges together.
"Sales skills are life skills. What make us better at sales makes us better in life. And vice versa." -Mahan Khalsa
Sales demands resilience, strategy, and a lot of patience.
With lengthy sales cycles, managing countless accounts, and piercing through layers of gatekeepers to reach key decision-makers, it’s no wonder that staying motivated often feels like trying to sail against the wind.
Yet these challenges offer powerful opportunities for growth, success, and fulfillment.
Whether you're an account manager, an SDR in a corporate or startup environment, a GM running your own business, or a consultant managing your practice, one truth remains: sales is one of the important part of your business.
Let's dive in.
A Marathon, Not the Sprint
Enterprise sales are known for having long sales cycles—some deals can take months or even over a year to close. This unrelenting timeline, paired with high-stakes targets and an endless stream of leads to nurture, can feel overwhelming.
How to Manage Lengthy Sales Cycles
Set clear goals and purpose. Take the time to define what you want to achieve and why it matters. By having a clear direction, you can focus your efforts, make better decisions, and stay motivated throughout the process. Clarity helps you prioritise and ensures that your actions align with your overall vision.
Prioritise High-Value Activities: With limited time, focus your energy on the clients and activities that can bring the most value. Remember, it’s not about doing everything but doing the right things. Focus on the RIGHT CLIENTS.
Success Story
One of my clients- a top sales, Nick, shared how he used to spend countless hours crafting pricing quotes for potential clients, hoping they would recognise the value of partnering with him. After diligently refining his qualifying process, he has since stopped wasting time—even on seemingly quick 10-minute pricing requests. Nick now appreciates the importance of protecting his "mental space." While 10 minutes might seem insignificant, it’s often enough to disrupt your focus and throw off your entire day.
Break It Down: Treat that monumental sales cycle like a marathon—set smaller, achievable goals along the way. Celebrate when you land a meeting, progress a lead to the next stage, or achieve a minor milestone. Choosing to walk away during the qualifying stage can be a significant victory. It allows you to focus your time and energy on the clients who truly matter.
Leverage Technology to Streamline Processes: Tools like CRM systems, Zapier workflows and AI-derived analytics help you identify high-priority leads and pinpoint where to focus next. Massive use case is using AI for research--A few weeks ago, I hosted a webinar on leveraging Perplexity for sales intelligence. Check it out here.
Success Story
Take Monica, a Senior Business Development Director who spent over 12 months nurturing her client through a particularly challenging cycle. Instead of seeing the time investment as a hindrance, she mapped out micro-goals, project -managed client stakeholders, celebrated small wins, and stayed proactive in communicating with her client. The result? A multi-million-dollar deal that propelled her career to new heights. Build buffer time into each stage of your sales pipeline.
Understanding your clients’ buying process is essential, as deals often progress more slowly than expected. Adding this flexibility ensures you’re better prepared and less stressed when timelines extend beyond what you anticipated.
Ask Yourself:
Am I targeting the right clients?
Do I have a solid strategy in place?
Do I fully understand what’s needed to achieve my sales goals?
Start by gaining clarity on these questions to set realistic and achievable objectives.
Breaking Down the Gates
Gatekeepers are part of the process in enterprise sales—whether it’s assistants, department heads, or internal bureaucracy—blocking access to a decision-maker is frustrating.
But your goal isn’t to bulldoze through these barriers; it’s to build trust, map stakeholders, and strategically bring decision-makers to the table.
Normalise dealing with gate-keepers.
How to Cut Through the Noise
Multi-Channel Approaches Work Wonders: Don’t focus on just one method of communication. Combine email, social media, phone calls, and executive round tables to stand out.
Conduct Pit-Stops: During my time at Alcatel-Lucent and Vodafone, we held regular pit-stops to evaluate and refine our strategies. As the Account Manager, I would present updates on account opportunities, decision-making processes, and key stakeholder relationships. These sessions let the team probe for gaps, ask questions, and validate our strategic direction. Most valuable of all, they help me execute a winning strategy.
Stakeholder Mapping: Know who influences decisions at every level, what needs to happen in every step and align your strategy.
Unique Value Propositions: Our clients don’t want a sales pitch—they want solutions to their specific challenges and unique situations.
Success Story
Consider another client-- a sales team navigating an organisation with over 20 layers of stakeholders. Instead of getting frustrated by gatekeepers, we developed a tailored engagement strategy by understanding each decision-maker’s priorities. We used a mix of LinkedIn outreach, phone calls, in-person meetings, and dedicated client workshops engaging senior leaders, they closed a breakthrough sale by developing credibility and trust.
Ask Yourself:
Who are the hidden champions (like mid-level managers) that can advocate for your solution internally?
Weathering the Storm
Enterprise sales pros know one thing for certain—the market never stands still. Customer needs evolve, industries change, and economic shifts create roadblocks. Staying adaptable isn’t just advisable; it’s vital.
How to Stay Relevant
Stay curious: Always keep an eye on market trends. Plug into industry webinars, white papers, and networking events to anticipate changes.
Ask questions: I always say this, securing meetings with our clients are precious opportunities, don’t just pitch the solution. Focus the conversation on understanding evolving pain points, goals or shifts in their strategies.
Be willing to pivot: Your prospects’ priorities can change mid-deal. Stay flexible in your approach and reposition your offering to meet their needs.
Tip:
When managing large, complex sales opportunities, it’s wise to start follow-up meetings by asking,
“Have there been any changes or updates to the project that I should know about?”
This simple question fosters clarity, ensures alignment, and keeps everyone on the same page.
Resilience isn’t just about holding out—it’s about bouncing forward. Use downtime or setbacks to hone your competitive edge, like finetuning your value proposition or enhancing your skills in negotiation.
Sustaining Motivation
Even the best salespeople face rejection, deals falling apart, and challenging targets. Keeping your spirits high can be the difference-maker in turning setbacks into success stories.
Tips to Stay Positive and Motivated
Celebrate Small Wins regularly to create momentum. Maybe you just completed the first demo call or had a positive interaction with a stakeholder—these moments matter.
Lean on Your Network: Share triumphs and frustrations with colleagues or peers in similar roles. Collaboration can uplift your perspective and inspire new strategies.
Set Micro-Goals: For example, “Secure three decision-maker meetings this month” or “Follow up with 10 leads this week.” These smaller wins will feel more achievable.
Invest in Self-Care: Burnout is a genuine challenge. To keep stress at bay, remember to take breaks, stay active, and engage in hobbies outside of work. Stepping away can rejuvenate your mind and sharpen your focus. For example, my recent weekend getaway worked wonders—it doesn’t have to be an elaborate vacation to make a difference.
Remember: You’re not a machine. Taking care of yourself is as important as taking care of your clients.
3 Keys to Becoming a Successful Enterprise Sales
We all strive for success—to overcome daily challenges and rise above them.
Enterprise sales isn’t easy, but its challenges make victory even sweeter. By managing lengthy sales cycles effectively, breaking past barriers to reach decision-makers, adapting to market changes, and maintaining a positive outlook, you can achieve remarkable results.
There are three habits worth cultivating on your enterprise sales journey.
Purpose. A clear goal and purpose fuels your motivation and creates a magnetic energy that attracts your ideal clients. When you come from an intention of helping your clients succeed, there is a mindset shifts. You focus on the right strategy and right clients.
Strategy is about making deliberate choices. When you develop a cohesive plan or theory that positions you on your chosen playing field with a clear path to victory, your chances of success significantly increase.
Resilience. Stay persistent, stay focused, and remember Zig Ziglar’s timeless saying: “You can have everything in life you want if you will just help other people get what they want.”
How do you manage your faith and motivation in your sales results? Where do you see it showing up in your work or life? Hit reply because I’d love to hear from you.
Thanks for being here, and I’ll see you next week.
Ren
PS:
If you’re ready to take your enterprise sales game to the next level, Book a Brainstorm session with me and let’s brainstorm a strategy for you and your team's sales success.
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