Introduction

When your business needs to shift from inbound to outbound sales to expand, how do you manage this transition? Where do you start, and where do you look for help? By leveraging senior executives and even your board, hiring dynamic SDRs, and creating structured business practices, your startup can sail through this transition and grow sales successfully.

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Key Takeaways and Calls to Action

Scaling a startup is no small feat, especially when it involves transitioning from an inbound to an outbound sales model. In our latest episode of "The Science of Scaling," Mark has a deep-dive with Carrie Bosworth, Senior Vice President of Sales at Checkr, to dissect the complexities and strategies behind building an effective outbound sales process. Carrie's extensive experience offers valuable insights and actionable takeaways for any startup looking to scale its revenue.

Her experience with sales starts from the ground floor. She worked as a sales associate and then as an account executive for Quest Software. She then moved up one rung to senior account executive with Salesforce and another when she became VP of Commercial Sales there. Moving to the digital presence platform Yext, Carrie applied all she knew to her roles as VP of global Midmarket Sales and then GVP of Commercial Business. Now an SVP with background checking company Checkr, she has brought all this experience from her own background to help the company scale and become a $2 billion unicorn.

These are the key takeaways from Carrie’s interview.

Mastering the Transition: From Inbound to Outbound Sales

Carrie joined Checkr with a mission to diversify their sales strategies, shifting from a predominantly inbound approach to a balanced model that emphasizes outbound activities. This transition isn't just about shifting focus; it involves restructuring teams, revamping strategies, and ensuring the entire organization is on board.

Understanding the Transition

Carrie explains that outbound selling is fundamentally different from inbound selling. While inbound leads often come with a smoother sales funnel, outbound requires meticulous planning, a rigorous routine, and an entirely different skill set. The transition starts with a keen understanding of existing gaps, followed by a deliberate plan to bridge them.

Key Takeaway 1: Understand the Skill Differences

Inbound selling usually involves responding to warm leads, people who have already shown interest in your product. In contrast, outbound selling demands proactive outreach to potential customers who may not be aware of or even interested in what you offer. The skill sets required are distinct.

Inbound Skills:

• Lead nurturing
• Quick response times
• Handling warm leads effectively  

Outbound Skills:

• Cold calling/emailing
• Persistence
• Strong research abilities
• Crafting compelling outreach messages

Building Operational Rigor

Transitioning isn't just about shifting focus; it's about embedding a new operational rigor within the team. Carrie spent her first 90 days with Chekr identifying gaps and another 6-9 months developing the outbound approach. This involved detailed planning and setting up the right books and processes.

Key Takeaway 2: Implement Operational Rigor

To ensure success, operational rigor is non-negotiable. This includes:

• Scorecards and KPIs: Regular tracking of outbound activities ensures that reps stay on target and identify areas for improvement.
• Structured Business Practices: Daily meetings, dashboards, and regular scorecard reviews help keep everyone aligned and accountable.
• Compensation Plans: Incentivizing outbound activities can maintain momentum and drive new logo acquisition. 

Messaging Strategy

Effective outbound strategies hinge on clear, compelling messaging. Carrie advocates for simplicity and authenticity in outbound messages. Targeting top accounts with personalized outreach ensures that your messaging resonates deeply with your prospects.

Key Takeaway 3: Craft Clear and Authentic Messages

A successful messaging strategy includes:

• Simplicity: Keep your messages straightforward and to the point.
• Authenticity: Be genuine in your outreach; no one likes a cookie-cutter sales pitch.
• Personalization: Tailor your messages to the specific pain points and needs of your top accounts.

Involving Senior Executives

Mark and Carrie emphasize the importance of involving senior executives in outbound messaging and strategy. Senior-level participation not only adds credibility but also aligns organizational goals with sales efforts.

Key Takeaway 4: Leverage Executive Involvement

Having senior executives involved can provide substantial benefits:

• Authority: Senior executives bring authority and can often open doors that junior reps can't.
• Alignment: Ensures that the sales strategy aligns with broader company goals.
• Strategy Development: Executives can provide insights and strategies that might not be apparent from a purely sales-focused perspective.

Hiring for Outbound Success

One of the most significant challenges in the transition from inbound to outbound is hiring the right talent. Carrie highlights the need for hiring leaders and reps with outbound experience.

Key Takeaway 5: Prioritize Outbound Experience in Hiring

It's crucial to onboard individuals who are well-versed in outbound sales. This involves:

• Experienced Leaders: Hiring leaders with a proven track record in outbound sales to guide the team.
• BDR Team: Building a BDR team with at least one year of outbound experience. Recruits from companies known for good training can be a good fit.
• SDR Roles: Hiring motivated, moldable new recruits, such as recent college graduates, particularly those with a background in college athletics, due to their inherent work ethic and determination.

Segmentation and Territory Planning

Effective segmentation and territory planning are crucial for successful outbound sales. Carrie Bosworth's approach at Checkr involves careful consideration of account size, industry, and team balance.

Key Takeaway 6: Execute Thoughtful Segmentation and Planning

Consider the following strategies for planning and segmentation:

• Account-Based Segmentation: Initially focus on account size and industry rather than geographic territories.
• Fair Book Distribution: Ensure that territories are divided fairly to avoid disparities among sales reps.
• Territorial Flexibility: Introduce extra territories at the start of the year to accommodate growth and ebbs and flows in market demands.
• Ideal Customer Profile (ICP): Base your ICP on Lifetime Value (LTV) rather than minimal Customer Acquisition Cost (CAC) to ensure long-term profitability.

Maintaining Flexibility

Flexibility in sales strategies and structures is essential. Mid-year disruptions can demotivate teams, so planning ahead and maintaining balance is critical.

Key Takeaway 7: Emphasize Flexibility

Ensure flexibility by:

• Supporting Sales Momentum: Avoid reshuffling territories mid-year to keep sales momentum.
• Pre-planning Territory Adjustments: Be prepared to adjust territories but assure reps that changes will be planned and communicated well in advance.

Utilizing the Board

Controlling outbound messaging and leveraging board members for connections and support can significantly amplify outreach efforts.

Key Takeaway 8: Leverage Board Connections

Board members can:

• Offer Credibility: Their involvement adds weight to your outreach efforts.
• Provide Connections: Board members can open doors and facilitate introductions that might otherwise be difficult to secure.
• Support Messaging: Their input can refine and support outbound messaging strategies.

Comprehensive Accountability

Accountability for both inbound and outbound activities is maintained through structured and regular reviews. This ensures reps are consistently performing at their best.

Key Takeaway 9: Maintain Comprehensive Accountability

• Regular Reviews: Conduct daily meetings and weekly scorecard reviews to keep track of progress.
• Performance Metrics: Utilize dashboards and KPIs to monitor performance and make necessary adjustments.
• Clear Expectations: Communicate clear expectations and provide consistent feedback to reps.

Long-term Planning and Growth

Lastly, long-term planning is essential. Crafting a career path for SDRs and ensuring continuous growth and development is key.

Key Takeaway 10: Focus on Long-Term Growth and Planning

• Career Pathing: Create clear career paths for SDRs to keep them motivated and invested in their growth within the company.
• Continuous Training: Invest in ongoing training and development programs to ensure reps are constantly evolving and improving their skills.

Conclusion

Transitioning from an inbound to an outbound sales approach is a complex yet rewarding journey. With insights from industry leaders like Carrie, startups can navigate this transition effectively, ensuring a balanced and scalable sales strategy.

Carrie's meticulous approach, from understanding skill differences to fostering flexibility and leveraging executive support, presents a comprehensive framework for success. Embrace these strategies, and you'll be well on your way to mastering the art of scaling your sales operations.

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Note: The insights shared in this podcast were initially distilled through advanced AI summarization technologies, with subsequent refinements made by the writer and our editorial team to ensure clarity and engagement.

About "The Science of Scaling" Podcast

Every week during a season, host Mark Roberge—co-founder and Managing Director at Stage 2 Capital and a senior lecturer at the Harvard Business School—interviews some of the tech industries most successful and renown leaders and managers in the areas of sales growth and Go-to-Market strategy. This is a HubSpot for Startups original podcast, and part of HubSpot's Podcast network. It's available on Apple, Spotify, and anywhere you get podcasts.