As a founder, you are used to doing whatever needs to be done to build your business – but this will quickly become a massive bottleneck for your startup. At some point, founder-led selling has to turn into structured sales. When this time comes, it’s time to hire your first sales leader. 

A few months back I shared some thoughts about what to look for in your first sales leader. Once you’ve hired your first sales leader, you’ve got some work to do. Setting the right goals and expectations can significantly impact your company’s trajectory. A successful relationship between you and your sales leader requires collaboration, clearly defined roles, measurable objectives, and shared business vision.

Understand Your Sales Leader’s Role

The first thing to do is to make an honest assessment of where your company’s sales currently stand. This means a deep dive into your current budget and sales progress, as well as corporate goals for at least the next year. 

Your sales leader is not just another hire. They are the linchpin of the success of the sales department. Their role extends beyond bookings and revenue, and involves building a formidable sales team, refining go-to-market strategies, and creating enduring customer relationships. This includes activities like drafting hiring and compensation plans, designing sales growth strategies (e.g.. geographic, vertical, etc.), zeroing in on target clients/segments, steering pivotal accounts, and making sure your team knows what it takes to meet or exceed customer expectations.

 When considering your first sales leader, remember that they come with a mix of curiosity and ambition. They will have pivotal questions – some of which you’ll face during interviews. So be prepared to discuss:

• Sales Process Ownership: Which components of the sales life cycle will they personally oversee? This could span from Market Research and Lead Generation to Qualification, Pitching, Closing deals, and Post-Sale Account Management.
• Team Building: Is there an immediate budget to build a team? If not, what’s the projected timeline and what metrics will drive decision making?
• Current Personnel: Are there existing team members championing certain sales functions? Will these individuals then report to the new Sales Leader? Be prepared to clarify organizational structure.
• Marketing Leadership: Who currently steers the marketing ship, especially in terms of strategy and budget allocation? Is there a possibility or even an expectation for these functions to fall under the new Sales Leader’s purview? (A quick note: tread cautiously here. Merging sales and marketing under one umbrella can sometimes muddle focus.)
• Operational Budgets: What monetary provisions are in place for travel & entertainment?
• Tech Stack: What CRM tools (like Salesforce, Hubspot, etc.) are the pillars of your sales processes? And more critically, will the sales leader have the autonomy to introduce or transition to new platforms?
• Revenue Goals: Clarify the revenue milestones. What benchmarks are expected in the ensuing quarters, or perhaps over the next year? What about longer-term, say over a three-year horizon?

Your answers to these questions help pinpoint the exact nature and qualifications of the leader you need. They assist in determining if you require a dealmaker, a team builder, or someone capable of developing and implementing a comprehensive market strategy – and help you set the right expectations from the very start of your interview process.

Being clear on the specific role they’ll play, along with the resources and budget available to them, sets the stage for defining their goals that align with your broader business aims. Given the quantifiable nature of sales roles, you have the opportunity to align your Sales Leader’s objectives with the company’s goals, ensuring they understand their responsibilities and are equipped to succeed in them.

Set Clear and Measurable Goals

Once you’ve selected the best candidate, you can then work with them to set appropriate goals. The SMART paradigm is a typical one used for structured goal setting. Here are sales-oriented examples. 

1. Specific: Your goals should be clear and well-defined. Instead of “increase sales,” a specific goal might be “hit a bookings target of $1MM in Q1, $1.2MM in Q2, $1.4MM in Q3 and $1.6MM in Q4”.
2. Measurable: You need a way to track progress and determine when the goal has been met. This could be through sales figures, hiring, new clients, or retention rates.
3. Achievable: While it’s good to aim high, setting unattainable goals can lead to frustration and lack of motivation. Your goals should be challenging yet achievable. This is especially important in sales as your sales leader will likely have compensation tied to achieving goals.
4. Relevant: Your goals should align with your overall business objectives and strategy.
5. Time-bound: Each goal should have a deadline or timeframe to maintain urgency and focus. Depending on your sales cycle and product, these could be monthly, quarterly, or annual.  Or all three!

Once you’ve set goals, communicate these expectations clearly and regularly. It is standard practice in professional sales to create a written sales plan with SMART goals carefully delineated, and compensation clearly defined based on hitting, and beating these goals. Take the time to explain the context and reasoning behind the goals and how they connect to your company’s strategy.  Ensure the sales leader knows the ‘why’ behind each goal and how they align with the larger company vision. Regular check-ins will help keep everyone on the same page.

Encourage your sales leader to provide regular feedback on their progress toward the goals and any challenges they are facing. Regular discussions can reveal obstacles and opportunities early on, allowing for timely adjustments.

Provide Necessary Resources and Support

Your sales leader is a vital part of your business success. To enable them to perform at their best, it’s essential to provide them with the right resources and consistent support. As discussed above, you’ve put together a plan, goals, tools, and a budget. But to succeed more is required. 

As your sales leader gets started, your partnership and guidance will be crucial for their success.  As they settle into their new position, they’ll rely on you to understand the specifics of your business, products, and sales strategies. Be prepared to train your sales leader and tag-team with them on sales calls. They will benefit from observing you during client meetings, gradually transitioning from watching to actively leading discussions and deals.

Your relationship with your Sales Leader is more than just functional; it’s about growth and development. As they become more proficient in their role, you’ll find yourself moving from the forefront to a supporting, advisory position. This shift will be influenced by various factors, including the intricacies of your products or services and the dynamics of the market. For complex products, you may need to be closely involved in sales discussions for a significant time – this could last for months or even years.

In short, your dedication to working closely with your Sales Leader, acting as both a manager and partner, ensures they are well-equipped and confident to lead sales initiatives on their own.

Adjust Goals and Expectations as Needed

Business dynamics are ever-changing, and goals might need to be reassessed and adjusted over time. Be open to reevaluating your goals based on market trends, business growth, or internal changes. The key is to maintain a flexible approach while staying focused on your overall business vision.

In Conclusion

Your first sales leader will play a pivotal role in your company’s growth and success. By setting clear, measurable goals and providing the necessary support and resources, you’ll be setting up a strong foundation for a productive relationship that drives your business forward. Remember, communication and flexibility are vital as you navigate this process.