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What makes a good startup head of sales?

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What makes a good startup head of sales?

Startups move to scale ups when they start to hit product market fit and are able to grease the wheels of their sales machine. Until that and, for a lot of companies, even after that startups often rely on a sales lead growth function. Success relies on not just an innovative product and agile product teams, but it heavily relies on effective sales strategies. Consequently, the Head of Sales becomes a key player, driving revenue growth and ensuring a smooth sales cycle. For startups utilizing Contract Sent, tailored for small to medium-sized tech startups, the Head of Sales gets a helping hand with the end of the sales pipeline, ensuring that things don’t get stuck in the ‘it’s with legal’ blackhole. Now, let’s explore what makes a good startup Head of Sales and how Contract Sent aligns with their needs.

1. Strategic Vision and Adaptability

A successful startup Head of Sales needs a strategic vision aligned with the company’s goals. They must navigate uncertainties, constantly adapting strategies to evolving market and customer needs. Contract Sent aids this process with a dashboard for contract negotiations, giving them the ability to have real-time monitoring and informed decision-making at the very tail end of their sales cycle.

2. Efficient Contract Management

Startups often face the challenge of time-consuming contract negotiations, significantly slowing down the sales cycle. The back and forth of these negotiations can drag out a sale far too long. The skills that a good head of sales has lay in their ability to help the team build relationships early on in the pipeline that will help speed this up. A good head of sales is able to enable their buyer to work as an educated champion and sell the need for their product into the customers wider team to create the buying tension needed to get things around the line.

3. Data-Driven Decision Making

In startups, where data, as long as it’s not garbage, will help you make better decisions and go faster. A successful Head of Sales leverages data analytics to track and measure the effectiveness of sales strategies.

These metrics go above and beyond the volume of sales that are being closed and the targets that are being hit. They get into to land of tracking the stages and the timing of those stages to forecast out three, six or twelve months ahead. This will allow sales teams to move from a couple of successful team members to full teams.

Contract Sent’s contract metrics dashboard provides valuable insights, enabling data-driven decision-making and optimizing the sales process.

4. Collaboration and Communication Skills

A good head of sales is characterized by exceptional collaboration and communication skills, which are pivotal for driving team success and achieving organizational goals. Collaboration involves working in tandem with various departments, understanding their needs, and aligning sales strategies accordingly.

This requires the head of sales to build relationships with team members and customers where there’s a level of open dialogue, mutual respect, and shared objectives. By leveraging the different parts of expertise within the company, the head of sales can create innovative solutions, streamline processes, and enhance overall efficiency.

Effective communication is equally important; it means that the individual has a clear articulation of vision, strategies, and expectations to the sales team, ensuring everyone is aligned and motivated. Regular feedback and open channels for discussion help in addressing concerns promptly and adapting strategies as needed. Moreover, excellent communication skills enable the head of sales to build strong relationships with clients, understand their needs, and provide tailored solutions that drive satisfaction and loyalty.

Internally, this leader must also communicate performance metrics, celebrate successes, and constructively address shortcomings to maintain a motivated and high-performing team. By showing these skills, the head of sales not only drives revenue growth but also builds a collaborative and communicative environment that propels the entire organization forward. In the end, the blend of collaboration and communication skills in a head of sales ensures cohesive teamwork, strategic alignment, and sustained success in a competitive marketplace.

5. Streamlined Approvals Process

A good head of sales can streamline the approvals process for contracts by implementing efficient workflows and leveraging technology.

First, they can standardize contract templates and establish clear guidelines, reducing the time spent on drafting and reviewing each contract. By integrating a centralized contract management system, they ensure that all documents are easily accessible and trackable, minimizing delays caused by miscommunication or lost paperwork. Automating routine tasks, such as electronic signatures and approval notifications, accelerates the process and reduces bottlenecks.

As well as this, the head of sales can be the glue for strong interdepartmental collaboration by clearly defining roles and responsibilities, ensuring that each stakeholder understands their part in the approval chain. Regular training sessions can keep the team updated on best practices and compliance requirements, preventing errors that could cause delays. By optimizing these processes, the head of sales enhances efficiency, reduces turnaround times, and ultimately accelerates revenue generation.

6. Comprehensive Contract Analysis

After a contract is signed, information is often trapped in a lengthy PDF. Addressing this pain point, Contract Sent provides an advanced contract comparison tool. Now, the Head of Sales can quickly analyze contract versions, facilitating a deeper understanding of terms and aiding in strategic decision-making.

7. User-Friendly Interface and Scalability

A good head of sales can scale a sales team by implementing strategic hiring, training, and performance management practices. They start by identifying the skills and qualities needed for success, ensuring they recruit top talent that fits the company culture.

Once onboard, new hires undergo comprehensive training programs that equip them with the necessary tools and knowledge to excel. The head of sales also establishes clear performance metrics and regularly monitors progress, providing constructive feedback and recognition to maintain motivation. As well as this, they promote a culture of continuous learning and development, encouraging team members to upskill and stay competitive. By always working to build a supportive environment and leveraging data-driven insights, the head of sales effectively scales the team to meet growing business demands.

The startup Head of Sales is one of the most important people for the success of the business, requiring a unique set of skills and tools. Contract Sent, designed specifically for tech startups, streamlines contract negotiations, helps people in this position kick off a good start for data-driven decision-making, and gives them a lever to pull in improving overall sales efficiency.


Contract Sent is not a law firm, this post and subsequent pages on this website do not constitute or contain legal advice. To understand whether or not the ideas and guidance on the Contract Sent website is applicable to your business, you should consult with a licensed attorney. The use and accessing of any resources contained within the Contract Sent site do not create an attorney-client relationship between the user and Contract Sent.

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