Back Button

The Importance of Creativity in Sales (With 8 Inspiring Examples)

Sales Training
Chris Orlob
March 19, 2024

Creativity is a crucial asset for sales teams who want to generate a consistent pipeline and achieve sustainable business growth. 

When done right, a creative sales approach can be a competitive advantage. It helps you build stronger client relationships and increase sales revenue and profit. 

If you’re looking to get better engagement and conversion from your sales process, read this practical guide on creativity in sales to get better results today. 

The article covers 5 key areas: 

  • What creativity truly means in sales (and what it does not)
  • Practical tips to include creativity into your sales process.
  • 8 inspiring case studies and real-world examples. 
  • How sales managers empower creativity in their sales teams
  • Essential tools and resources for creative sales professionals. 

Ready to take your sales game to the next level? join over 10,000 creative sales professionals who are consistently exceeding their quotas with our expert-led skill development programs. 👉Get Instant Access 🔥

What creativity in sales really means

In sales, creativity refers to the strategic combination of originality and innovation throughout your sales cycle. By using your creative thinking skills, you can apply unique and fresh ideas to various aspects of the process, from initial contact to closing the deal, ultimately sparking undeniable curiosity in your prospect.

Creativity empowers sales teams to overcome modern-day challenges in several key ways:

  • Standing out from the crowd: By crafting unique, attention-grabbing messaging, storytelling, and visuals, you can effectively cut through the noise and reach your target audience, leaving a lasting impression.
  • Solving customer problems creatively: Creativity allows salespeople to dig deeper into customer needs and challenges. This enables them to tailor solutions, discover unconventional ways to add value beyond just the product or service itself, and ultimately achieve greater customer satisfaction.
  • Building stronger relationships: A creative sales approach fosters meaningful connections with clients by going beyond the typical sales pitch. This requires empathy, emotional intelligence, and the ability to connect on a more personal level.

While creativity is crucial for engaging today's buyers, it thrives alongside a strong foundation in sales fundamentals. It's equally important to understand the boundaries of creativity in sales to ensure ethical and effective implementation.

What is not considered creativity in sales

  • Manipulation: Earning a meeting through genuine curiosity about your potential customer's needs is far more effective than tactics that rely on emotions like sympathy or guilt. Remember, long-term success hinges on building trust, not exploiting emotions.
  • Empty Gestures: While creative outreach can be valuable, it needs substance. Lavish gifts like champagne bottles may grab attention, but they lack genuine value and can backfire. Focus on showcasing your expertise and unique value proposition in engaging ways.
  • Short-Term Wins: True creativity fosters lasting connections. Avoid tactics solely aimed at quick gains, as they don't build trust and hinder long-term partnerships.

Practical tips to include creativity into your sales process

Here are some ideas on leveraging creativity for pipeline development from strategy through execution.  

Prospecting and outreach:

The following are examples of how you can target potential customers with creative solutions in the prospecting stage. 

  • Creative Referral Strategy: Leave business cards in marketing stands at existing clients' offices. Offer referral credit if clients recommend you when visitors pick up a card. This passively generates referrals as clients discuss your services with visitors.
  • Engaging Video Cold Calls: Ditch email spam! Record personalized, 1-2 minute videos for each prospect. Upload them as unlisted YouTube videos and send them with a personalized subject line. While email filtering is possible, YouTube improves deliverability and potentially increases response rates.
  • Personalized Gifting: Send a custom-made gift related to the prospect's interests or industry. This sparks curiosity and opens the door for conversation.
  • Interactive Content: Create quizzes, surveys, or games that assess the prospect's needs while providing relevant information about your offerings. This engaging approach helps you connect with potential customers while generating valuable insights.
  • Unique partnerships: Collaborate with non-competitive businesses to reach new audiences and offer bundled solutions. The Microsoft and Adobe partnership exemplifies how creative partnership increases sales. 

Presentations and communication:

  • Speak the Customer's Language: Analyze your CRM for keywords like "problem" from past interactions. Use these authentic customer statements in your presentations and demos to increase engagement.
  • Listen for Pain Points and Customer’s Specific Needs: Shift your focus from solution statements voiced by prospects ("We need X to achieve Y") to identifying the underlying problems ("We risk losing revenue if Z doesn't improve"). Understanding the difference can be the key to overcoming pricing objections.  
  • Move Beyond Features: Don't just list benefits; create compelling business value cases that quantify the impact of your offering using clear and engaging visuals like charts, graphs, and infographics.
  • Go beyond a one-size-fits-all approach. Develop unique strategies that address the specific needs and challenges of each customer. Consider a consultative selling approach– your prospect’s problems should lead to a solution. 
  • Crafting a creative sales pitch: Your prospect already knows your sales pitch covers multiple ways your product/service can create value. To keep their curiosity locked in, include creativity in your sales pitch. Don't just say your prospect will save $10,000 annually; show them how that translates to relatable outcomes.
  • Connect Emotionally: Use impactful stories (remember, people recall stories, not statistics) to illustrate your product's value and connect with buyers on a deeper level.
  • Interactive demos: Ditch static presentations! Offer interactive demos, simulations, or even virtual reality experiences to let prospects actively engage with your product.
  • Humor: Use humor strategically to build rapport, make your message memorable, and ease tension. Remember, the goal is to cultivate trust and respect while creating a welcoming atmosphere.

Closing the deal and building relationships:

  • Animated customer success stories: Go beyond traditional case studies; create engaging animated customer success stories that resonate emotionally with prospects. This makes complex solutions easier to understand and builds trust.
  • "Wow" moments: Implement unexpected gestures like handwritten thank-you notes, exclusive feature access, or personalized recommendations to build stronger relationships with customers.
  • Customer success stories: Showcase the impact of your offering by sharing customer testimonials and case studies, building trust and demonstrating value.
  • Community building: Establish a forum or event where customers can connect, share best practices, and feel valued, fostering long-term relationships.
  • Flexible solutions: Be willing to tailor your offering and payment terms to meet each customer's specific needs. See how to negotiate discounts creatively
  • Inject creativity in your follow-up sequence: Instead of generic reminders, craft follow-up emails that offer additional value, like highlighting previously unmentioned contract guarantees. This incentivizes decision-making and demonstrates your commitment to the customer's success.

8 creative sales success stories to inspire you

The following are examples of creative sales professionals achieving sales success.

  1. Gong and the Old Spice Guy 
  2. Unqork: The $ 2 billion enterprise tech that never sends RFPs
  3. Roam’s founder-led sales (a contrarian approach)
  4. Yext; when advisors become BDs.
  5. John Patterson and the Dummy Register
  6. Conor McCluskey’s BombBomb– from pain point to profit
  7. Brex’s targeted outreach, creative campaigns and Champagne bottles. 
  8. The Sales Rebel: Crumpled Letters, Curiosity, and Connection. 

1. Gong and The Old Spice Guy

When Sarah Brazier, account executive at Gong, couldn’t get a hold of an enterprise prospect. She got one of the trendy-hot celebrities to record a personalized sales video for the prospect– and closed the deal. 

Initially, Sarah sought to create a humorous spoof ad featuring former NFL player and Old Spice commercial star Isaiah Mustafa, promoting Gong as "The rep your rep could sell like." However, limitations prevented this specific execution. Yet, Sarah's research revealed Mustafa's background in sales, sparking a new idea.

Instead of focusing on a broader brand message, 

  • Sarah personalized the video message by requesting a Cameo from Mustafa specifically for Plixer. 
  • She then seamlessly integrated this personalized video into her outreach sequence through Drift, a platform that tracks video opens. 
  • Emailed the prospect explaining why she believed a conversation would benefit Plixer.

That way, she offered relevant value and opened the door for potential engagement.

This case study illustrates the effectiveness of creative and personalized outbound sales outreach in grabbing attention and building relationships.

2. Unqork: The $ 2 billion enterprise tech that never sends RFPs

Traditionally, lengthy RFPs and generic proposals often create an impersonal and cumbersome experience for software buyers and sellers. Unqork, a no-code application platform, broke this mold and revolutionized the sales process.

Recognizing the speed and flexibility of its platform, Unqork embraced hyper-personalization as its core sales strategy. Instead of relying on traditional RFPs and lengthy proposals, they focused on crafting a highly personalized customer experience.

Here’s what they did:

  • Targeted Approach: Unqork meticulously targets specific industries like banking, identifying companies facing common problems like customer onboarding.
  • Direct Engagement: Unlike generic marketing materials, Unqork representatives directly meet with target customers, inviting them to experience the platform firsthand.
  • Live Demonstration: Utilizing the platform's drag-and-drop functionality, Unqork representatives collaborate with potential customers to build real-time customized solutions. This live demonstration showcases the platform's capabilities and addresses specific needs within minutes.

This unique sales approach has yielded impressive results for Unqork– with over $ 2 billion in valuation. By bypassing lengthy proposals and showcasing the platform's capabilities through a personalized and interactive experience, Unqork:

  • Demonstrates Value: The live demonstrations provide tangible evidence of the platform's ability to solve specific customer problems.
  • Increases Engagement: The interactive experience fosters deeper engagement and allows existing customers to visualize their specific needs being addressed.
  • Reduces Time to Value: By showcasing the platform's rapid solution-building capabilities, Unqork streamlines the sales cycle and accelerates the time to achieve customer value.

Unqork's hyperpersonalized sales strategy demonstrates the power of tailoring the sales process to match each customer's unique needs. 

3. Roam’s founder-led sales (a contrarian approach)

Founder-led sales is a brilliant and innovative approach that can revolutionize your sales strategy. Roam adopts a contrarian top-down method instead of following the traditional bottom-up approach where junior staff pitch to higher-ups. 

The founder, Howard Lerman, gets on the phone with the founder and has them implement the software with the entire company.

Here's why it's so effective:

  • Increased Stickiness: When a founder personally champions a product within their company, it creates a sense of ownership and commitment. Founders have a vested interest in the success of their company, so they're more likely to ensure the product is fully integrated and utilized throughout the organization. This increased involvement leads to higher retention rates and stronger customer loyalty.
  • Eliminates Future Selling: When a founder becomes your champion, you bypass the need for future selling efforts. Founders are intimately involved in the decision-making process and are invested in the product's success. Once they're on board, the rest of the company will likely follow suit, eliminating the need for additional sales pitches.
  • Access to Senior Decision-Makers: By engaging with founders directly, Roam gains access to the highest levels of decision-making within companies. Senior executives have the authority and influence to quickly implement changes throughout the organization. By leveraging this direct line to senior decision-makers, Roam streamlines the sales process and accelerates conversion rates.

Roam’s founder-led sales effort is a smart and creative sales strategy that prioritizes building relationships at the highest levels of organizations, ultimately leading to greater success and faster growth.

4. Yext; when advisors become BDs.

By strategically constructing a board of advisors, Yext unlocked a pathway to effortlessly accessing decision-makers.

Howard Lerman, founder of Yext, understood that when your advisory board consists of individuals with connections and influence within your target market, you gain direct access to key decision-makers. 

When he started Yext, Howard wanted to sell to gyms. He contacted the founder and president of URSA– the trade organization for gyms– and made him an advisor to Yext. 

That strategy helped Yext sign up every gym because the advisor just made a phone call– as he was a phone call away from everybody.

What’s more? 

The strategy costs almost zero dollars upfront. These advisors are often enticed by stock options and are motivated to contribute their expertise and connections to your company's success. 

This approach generates leads and creates demand as advisors utilize their networks to open doors for your sales team.

5. John Patterson and the Dummy Register

In the late 19th century, cash registers were a novelty, often unreliable and expensive. A driven salesman, John Patterson saw the potential in NCR's cash register but recognized the need to overcome customer resistance.

So, he developed a structured presentation method and focused on in-person product demonstrations. Here’s what he did

  • Structured Approach: Patterson created the "Four Steps to Sale" framework: Approach, Proposition, Demonstration, and Close. This ensured consistent and organized sales interactions.
  • Scripted Presentations: He developed detailed scripts for each step, focusing on building rapport, identifying customer needs, and highlighting the product's benefits.
  • Engaging Demonstrations: Unlike simply describing the register, Patterson emphasized live demonstrations showcasing its features and benefits in action, making the product more tangible and engaging for potential buyers.

The dummy register is an example of using a real-life demonstration to sell cash registers. 

To overcome objections about cost, Patterson created a non-functional, wooden cash register model. Salespeople used it to demonstrate key features and benefits without needing the product, making sales calls more convenient and impactful.

NCR became the leading cash register manufacturer, demonstrating the success of Patterson's innovative approach. Additionally, Patterson’s "NCR Model" became a blueprint for modern sales training, influencing generations of salespeople and managers.

6. Conor McCluskey’s BombBomb– from pain point to profit

Connor McClusky faced the challenge of scaling his billboard sales approach. While analyzing his sales strategy, he realized that spending more time with existing clients positively impacted renewals and reduced the need for extensive prospecting. 

However, physically visiting every client every month was not feasible. He questioned, "What if I could send a video through email?"

Unable to find a solution, McClusky created his video messaging platform. Leveraging his understanding of the SaaS model, he collaborated with a video professional to develop a simple message thanking existing clients.

The initial video email campaign, sent in 2006, yielded immediate and unexpected results. Within 48 hours, McClusky received a wave of positive responses, praising the video itself and inquiring about the tool used. Clients were fascinated by the novelty and effectiveness of video communication.

This example showcases the power of creative problem-solving and capitalizing on market gaps. By identifying a personal need and recognizing its potential application for others, McClusky solved his sales challenge and established a thriving business built on hyper-personalized video communication. 

7. Brex’s targeted outreach, creative campaigns and Champagne bottles 

Brex, a company offering corporate cards and financial software for startups, adopted a multi-pronged approach to acquire new customers, prioritizing targeted outreach and unique engagement tactics.

Leveraging Warm Introductions:

  • 1st-degree connections: Brex initially focused on connecting with individuals within their ideal customer profile (ICP) through existing 1st-degree LinkedIn connections. This included founders and finance professionals at early-stage startups.
  • Investor network: They further benefited from their investor network, specifically their partnership with Y Combinator (YC), a prestigious startup accelerator. This allowed them to access companies within their target market and leverage introductions from other investors to their portfolio companies.

Transitioning to Creative Outbound Strategies:

Once they exhausted warm introductions, Brex transitioned to more creative outbound campaigns:

  • Champagne campaign: They sent personalized champagne bottles and handwritten notes to a targeted list of several hundred companies in the Bay Area. This personalized approach offered a higher engagement probability than traditional mass email sequences.
  • Targeted billboards: Brex strategically placed billboards throughout San Francisco. They then implemented targeted email campaigns to individuals near the billboards, leveraging the increased brand awareness to improve email response rates compared to those unfamiliar with the company.

Brex's customer acquisition strategy effectively combines targeted outreach with creative engagement tactics. By leveraging existing connections, personalized approaches, and strategic marketing initiatives, they successfully reached their target audience and acquired new customers.

8. The Sales Rebel: Crumpled Letters, Curiosity, and Connection

Dale Drupee, founder of The Sales Rebel, emphasizes the power of creating memorable experiences to capture prospect attention and book meetings. One of his unique methods is the "Rebel Letter Campaign."

Here’s how it works: 

  • Send themed letters: These are deliberately designed to look unconventional, often crumpled or adorned with stamps suggesting they've "traveled the world" to find the recipient. The message is clear - most sales and marketing materials are ignored, so this one embraces humorously.
  • Personalized message: The letter acknowledges the recipient's busy schedule and offers a brief, relatable message. For example, it might say, "You're probably wondering why this is crumpled up. Well, 90% of sales and marketing is trash. So I pre-crumpled it to make it easier for you to throw away..."

Why does this work?

  • Standing out from the crowd: The unconventional design grabs attention amidst the typical marketing clutter.
  • Humor and relevance: The self-deprecating humor and relatable message spark curiosity and engagement.
  • Intriguing details: The crumpled letter and handwritten elements pique interest, prompting recipients to want to know more.

By sparking curiosity and offering a novel experience, the Rebel Letter Campaign increases the likelihood of positive responses and successful phone conversations when following up with prospects who received the letter. This example highlights the importance of creativity and personalization in the sales process. 

How to empower your sales team’s creativity

  1. Developing creative sales professionals through training and coaching
  2. Encouraging adaptability and risk-taking in sales strategies
  3. Treat creativity like a potluck dish.
  4. Embracing experimentation is the key.
  5. Leverage emotional intelligence and problem-solving

Research has shown that manager empowerment can increase a salesperson’s creativity. When managers create an enabling environment, the bullpen is empowered to take more risk, be innovative and ultimately, get creative with sales. Here are specific ways sales managers can empower sales professionals to apply creativity in sales. 

Developing creative sales professionals through training and coaching

Sales leaders should understand that anyone can become more creative when exposed to sales training and coaching programs that:

  • Expose them to diverse ideas, 
  • Helps them replace best practices with better techniques
  • Improves their willingness to experiment with practical and result-driven tips. 

For example, a training program like Pclub’s SaaS discovery masterclass teaches sales reps to get creative with questions to uncover business pains that money follows. Through techniques like role-playing sales teams would learn new discovery models and training that represent how today’s B2B buyers want to be sold to. 

Encouraging adaptability and risk-taking in sales strategies

Traditional sales tactics can become predictable and lose effectiveness over time. Encouraging adaptability empowers salespeople to think outside the box and develop new approaches tailored to specific situations and customers.

Sales leaders can adopt the following techniques:

  • Set sales targets around creative outputs: Besides hitting their daily or monthly metrics, such as sending 55 emails per month, try encouraging reps to get an email response that says, “this is the best marketing or sales call I've ever gotten in my entire life.” Or encourage AEs to get 5 prospects to laugh on discovery calls.  
  • In a junior position, get someone new to take the call: They are eager to bring some value to the organization and have more time. Before they learn the best practices, get a scoop on how they run sales calls naturally. You might be surprised. 

Treat creativity like a potluck dish

Like a potluck thrives on diverse contributions, fostering creativity in your sales team requires collaboration. 81% of sales representatives say team selling helps them close deals, according to Salesforce. 

Sales managers can encourage this collaborative spirit by: 

  • Embracing a sales enablement mindset where reps collaborate with creative minds in other departments. 
  • Providing the necessary tools and resources to support team members in their creative endeavors, from interactive training sessions to access to cutting-edge technology. 
  • Implementing a mutual success plan that reinforces a shared goal and collective achievement.

Experimentation is key

Encourage risk-taking and experimentation within your sales team. Celebrate failures as learning experiences and reward successful creative endeavors. Not every creative idea will be a success. The goal is to develop your team’s sales acumen, not close every sale without fail. Creativity in sales requires taking risks and being willing to fail fast and learn from those failures. 

Leverage emotional intelligence and problem-solving

The reality of modern sales is that we need to understand individual behavior better and apply that understanding to our engagement techniques. High emotional intelligence allows salespeople to read emotions, empathize with prospects, and tailor their approach accordingly. This emotional connection lays the foundation for creative solutions that resonate with customer needs. 

Tools and Resources for Creative Sales Professionals


LinkedIn is a great place to start if you’re looking to use social media as a creative sales tool. Aside from the general features, LinkedIn’s video emails are a game-changer. Unlike emails, where your video pitch can get lost in the spam folder, you can directly send sales videos to your first-degree connection as a direct message. 

Video messaging software

Video messaging software like Cameo, Loom, and others are valuable tools for creative sales professionals because they:

  • Add a human touch to your outreach
  • Increase engagement
  • Offer flexibility and convenience: Recording a short sales video is faster and easier than writing a lengthy email copy. 
  • Showcase personality and expertise: Videos allow salespeople to showcase their personality and expertise, making them more relatable and credible. 

Free lead generation and nurturing resources

Take advantage of Pclub’s free lead generation and lead nurturing resources to inject creativity into your sales process:

Find more free sales templates, cheat sheets, and resources here. 

Sales intelligence software

Sales intelligence software empowers creative salespeople by providing data-driven insights on prospects and market trends. This fuels targeted outreach, sparks innovative solutions by allowing tailoring to specific customer needs, helps prioritize efforts for high-impact opportunities, and keeps them ahead of the curve by anticipating market shifts.

Level up your creativity in sales with Pclub

Tired of missed opportunities and unresponsive prospects?

Ready to join over 10,000 creative sales professionals crushing their quotas?

Pclub provides cutting-edge sales training curated by the top 0.01%, giving you the edge you need to succeed in today's competitive landscape.

Learn from the best:

  • Ditch outdated tactics: Master the latest strategies for connecting with modern B2B buyers.
  • Shift your focus: Move beyond features and benefits to truly understand customer pain points.
  • Win more deals: Develop a compelling value proposition that sets you apart from the competition.

Pclub equips you with the skills and knowledge to:

  • Spark genuine curiosity: Engage prospects with innovative approaches that address their specific needs.
  • Build lasting relationships: Foster trust and connection through genuine communication.
  • Achieve sustainable success: Master the fundamentals while remaining at the forefront of sales innovation.

Ready to take your sales game to the next level? 👉Get Instant Access 🔥

Profile picture of Alex Moffitt
Profile picture of Alex Moffitt

Want me (and other top sales practitioners) to train your sales team?



Six 'Underground' Sales Techniques We Used to Grow Gong from $200k to $200M in Five Years. This 60 min training has been WIPED CLEAN from the Internet... and can be yours for $7.

​​​​​​​Plus, how I grew my personal income from $36,932 to $1,639,982 in nine years.

Claim Exclusive Access For $7


10 Proven Scripts, Questions and Talk Tracks to Turn Discovery Calls Into Customers.

These 10 scripts are the secret to  creating a repeatable selling system that just about anyone selling SaaS to a business can use to achieve repeatable sales success.

Yes! I'm Ready to Get Started

FREE: 10 Scripts to Close More Deals Faster and Easier Than Every Before

Claim your copy of the “Underground Closing Motion Scripts eBook, FREE For a Limited Time

In this free guide, you’ll find the most powerful closing motion techniques (which yes, involves exact words, scripts, and questions along the way) that I’ve learned for closing deals, managing the “last stretch” of a deal, and closing deals faster and on time.

Yes! I'm Ready to Get Started