Secrets to #InsideSales Interviews from Industry Leaders

Secrets to #InsideSales with @MarkRoberge Formerly @HubSpot Currently @HarvardHBS

1. In your book, The Sales Acceleration Formula, you identified 5 traits of a highly successful HubSpot sales rep. How important is it for inside sales leaders approaching scale to identify their traits of a high-performer? How early on should they identify these traits?

You’ve already learned about the traits we looked for to identify top performing reps during the growth stage of HubSpot: coach-ability, curiosity, intelligence, work ethic and prior success. We would analyze every rep against these traits from the interview stage through onboarding and would let them go if they were not a good fit. While the formula is different for every organization, the process is the same. You should identify traits of a high performer as soon as your product is ready to sell.

Every rep that you hire who does not work out greatly impacts your bottom line. I would recommend that you have a process in place where both you and the founders have agreed on a set of criteria before making your first sales hire. Test. Learn. Iterate. It will be comforting to have this muscle group developed as you enter years when you need to hire dozens of new salespeople.

2. With an engineering background, you were able to leverage data and science to grow from $0 to $100M in ARR. What advice can you give to an inside sales leader with no engineering experience to become more data-driven?

As a sales leader, you are tasked with one of the most important roles in growing a business regardless of resources, experience or skill level. Without a pipeline and a constant stream of revenue, your business will die. I was fortunate enough to have a background in engineering which prepared me with the analytical and scientific skills needed to establish a results-driven sales machine. However, I was also fortunate enough to work with a team who believed in leveraging data to drive performance from the marketing side. This combination was a true recipe for success.

So how can you, as a sales leader with no engineering background, replicate this type of scientific sales process? First, I do not think a strong analytical mindset is necessary to succeed. Simply surround yourself with a support team that addresses your weaknesses. If you are not a quant, hire a sales ops “right-hand-person” as early as possible. Also, read, learn and replicate what other successful teams have already achieved. Having at least some foundation will help you hire and manage your ops partner. There are a ton of resources out there to help guide you through this process. Here’s some great resources to get you started:

  • My book, “The Sales Acceleration Formula
  • Sales Hacker is filled with great inside sales content
  • Of course, the HubSpot Sales blog is a great resource

3. Most of the inside sales process is typically automated for high-growth teams. What part of the inside sales process should NOT be automated?

You may be surprised, but I believe there are many, many facets of building and scaling an inside sales team that do not rely on data, technology, and automation. For example, on the personal selling front, building trust and uncovering unique buyer needs is very difficult to automate. On the leadership front, diagnosing salesperson coaching needs and devising a coaching plan based on the reps deficiency and learning preferences is impossible to automate. I can go on and on.

The “automation” and “technology” movement in the past few years has shown us that aspects of selling and sales management can do a much better job of leaning into data and technology to yield new efficiency gains. However, there are still many execution areas that rely on factors outside of these tools.

Key Takeaways

  • Develop your hiring process for sales reps early on before your team scales up. Every hire can impact your bottom line.
  • Ensure you have a sales culture that is results driven. Learn from the best and surround yourself with a support team that addresses your weaknesses.
  • There will always be processes that can’t be automated. Building trust and uncovering your buyers needs can’t be automated. At the same time, leading a team and developing a customized training program will never be automated.
The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million

The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million

Use data, technology, and inbound selling to build a remarkable team and accelerate sales. The Sales Acceleration …
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Secrets to #InsideSales with @DougLandis of @BoxHQ

1. When you were the VP of Sales Productivity at Box, you managed to successfully onboard inside sales reps during times of hyper-growth. What onboarding processes were key to providing reps with the tools, skills and knowledge they needed to be successful?

Productivity is the backbone of any successful sales team and it should be the number one focus during periods of growth. It’s easy when you’re a startup to just go “hog wild” and change things on the fly. However, as you grow it quickly becomes an essential part of your business to get new hires up and running faster, as it directly impacts your bottom line. My customers are the internal sales folks and it’s my job to make them successful.

At Salesforce, I onboarded around 8,000 reps during my time there and I quickly realized how important it is for a sales leader to be able to identify top performers early on. If you can’t do this, you are throwing money away. In order to identify your top performs and get reps up and running faster, a successful onboarding program should at least cover these areas:

Core elements:

  • Do they understand the company messaging?
  • Can they successfully pitch and demo the product?
  • Do they understand our industry (competitors, landscape, trends, etc.)?

Sales process:

  • Do they know what makes a great seller great (at this company)?
  • Can they adopt this process to move a deal forward?

System and tools:

  • Do they know how to use our CRM?
  • Can they successfully use the tools to be more productive?


  • What’s their level of knowledge before getting started?
  • Have they grown over the first week, month or quarter?

2. You’ve probably heard the phrase, “teams who sell together, win together.” How have you created a culture of collaboration between your inside sales reps and the rest of your organization?

When it comes to sales collaboration, I like to think about it in two different buckets:

Team collaboration: Team collaboration consists of the sales team you’re on, such as the region or vertical that you sell to. Every team has their own culture which is driven by the front line managers. I believe the front line managers are the most forgotten about yet most valuable manager in the organization. They are in the trenches helping the team be successful. This type of collaboration is really important for day-to-day success. This collaboration drives healthy competition and supports comradery among the folks you’re interacting with every single day.

Company collaboration: We use to always say, “you never win a deal or lose a deal alone” at Salesforce and this is the perfect way to think about company collaboration. Company collaboration is all about getting the right people involved in a deal at the right time, you should never try taking a deal down by yourself because it’s too difficult to do. Every single deal involves multiple people on your team: engineering, product, customer success, executive sponsor, etc. You have to understand who in your organization you can rely on and connect with for each deal. If you have a customer who is concerned with security, you need to get your security person involved in the deal and you need to build real relationships with them over time. These types of relationships create true company collaboration and ultimately improve sales performance.

3. Most of the inside sales process is typically automated for high-growth teams. What part of the inside sales process should NOT be automated?

I’m old school, I come from the days of working at Oracle and making 100 phone calls a day. In my personal opinion, lots of these new automated tools are making sales professionals lazier by relying too much on emails. There needs to be a better balance between phone calls, emails and social interactions. Getting in front of the right person who can move a deal forward means being proactive and there’s no way to automate this.

Selling is a numbers game. It’s about persistence, relevance, timing and understanding who your buyers really are. There’s just too much noise out there, and automation will not create the personalized interactions that you need to be having. Your buyers can easily tell if your interactions are automated and with one simple mistake, you could kill the deal.

Key Takeaways

  • Productivity is the backbone of any successful sales team and it should be the number one focus during periods of growth. Develop your onboarding process early on and ensure it covers all of the key areas to identify top performers.
  • Team collaboration within a sales team is incredibly important to improve day-to-day performance and is driven by the front line manager – the most valuable manager. Company collaboration is all about leveraging the right experts in your organization to help educate the buyer and remove their concerns.
  • Getting in front of the right person to move a deal forward requires you to be proactive – this can’t be automated. Creating those personalized engagements that need to happen can’t be automated and your buyer can easily tell what’s automated. Automation can kill a deal with one simple mistake.
The Only Sales Guide You’ll Ever Need

The Only Sales Guide You’ll Ever Need

“Contrary to what most underperformers claim, sales success is not situational. It’s not about the market, the product, …
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Secrets to #InsideSales with @elleskala Formerly @Influitive Currently @DigitalOcean

1. You led sales at Influitive to their first $10M in ARR – this is huge! How do you think about the balance between inside sales and field sales reps during this stage of growth?

First of all, I don’t actually believe in the distinction between “inside” and “field” sales reps in today’s world of selling. Everyone is a hybrid, regardless of their experience. It’s also less about the size of your company and more about the product you are selling which determines the right balance. If it’s a straightforward sale, doesn’t require a buying committee and/or isn’t disruptive, you should focus more on leveraging technology to help you sell better and faster.

However, if your sale requires face-to-face conversations and there’s multiple buyers from various departments, you need to find field reps. It’s important to think about a rep as a hybrid, as most deals are not that clear cut. If you’re good at using technology but need to jump on a call to close the deal, you do whatever needs to be done. Leverage your strengths as they align to the buying process.

2. You have an incredible amount of sales experience at hyper-growth organizations across enterprise, inside and channel sales, sales enablement and operations. How is building a scalable inside sales team different from the rest?

If your sales process is repeatable and you are able to leverage technology to successfully scale up, it does require very different performance metrics than someone who is selling large, complex deals. Inside sales metrics can be measurable and optimized to the extreme, especially selling in today’s world with so many tools available. You might be looking at email open rates, response rates, meetings sets etc. on a daily basis.

On that same point, those reps who are leveraging technology and have a repeatable sales process must continuously be trained. When I was leading an inside sales team of 60+ people, we did 2-3 hours of training every day with 1 manager for every 6 reps. You have to make sure that every rep is doing each and every step to move a deal forward, even something as simple as following up by email after a phone call. Of course, building and growing a team like this is very different from field reps.

3. Most of the inside sales process is typically automated for high-growth teams. What part of the inside sales process should NOT be automated?

In my opinion, inside sales is already over-automated, like everything else. I believe we are losing the art of conversation and there is already a correction happening where reps are realizing the need for phone or in-person conversations to truly connect with their buyers. You simply can’t have a real conversation over email or by chat. We need to pick up the phone more and talk to our customers. Although I’m not a fan of automated emails, I do think technology can improve the quality of our conversations without replacing them. This is exactly what I’ll be talking about at HubSpot’s Inbound Conference this year in my presentation, “The Lost Art of Conversation” and you can read more about it in this Talkdesk article.

Key Takeaways

  • Don’t always try to make a distinction between inside reps vs. field reps. Sales professionals today will be a hybrid depending on how complex your offering is.
  • Building an inside sales team requires a metrics driven approach in order to continuously optimize. It also demands a lot of training to ensure reps are doing every step required to move a deal forward.
  • Inside sales is already over-automated. Technology should help us have better conversations with our buyers, it should never replace the conversation. Meet your buyers or talk with them on the phone to truly understand their challenges.
Solution Selling: Creating Buyers in Difficult Selling Markets

Solution Selling: Creating Buyers in Difficult Selling Markets

Solution Selling is the most comprehensive sales and sales management process available today.
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Secrets to #InsideSales with @LiamSurridge Formerly @SAP Currently @Hootsuite

1. You have a ton of experience leading large inside sales teams from your days at SAP to now at Hootsuite. What’s the biggest difference between leading an inside sales team today and what it was 5 years ago?

The acceptance of inside sales as an optimal route to market by our prospects and customers, which is both an asset and a minor challenge. One of the biggest changes is the increase in the number of inside sales teams out there today. Back in 2002, inside sales was still a relatively new route to market for medium to complex enterprise selling, and the tactics we used were far less adopted across sales organizations.

During the early days we had a lot of success since buyers were more receptive to inside sales techniques, i.e. phone calls, voicemail and email marketing. Today, there are potentially thousands of inside sales teams and it’s becoming increasingly difficult to reach customers on first contact, or ever, since many organizations use very similar techniques. I make the assumption that it is a much noisier world for our prospects today than it was even a few years ago – it requires we bring far greater value to our outreach than in the past.

On the other hand, prospecting has become much easier for the average rep with the explosion of social data through networks like LinkedIn and Twitter. It’s much easier to learn about your buyers and quickly identify ways that you can provide value to them in order to develop those relationships. With access to all of this data, you can work to earn a “trusted advisor” status much easier if you actually take the time to do the research and learn their business. With all of this data comes a new generation of tools designed to help reps get better, faster insights about their buyers.

2. While leading a team of 40+ inside sales reps, you must see a wide range of capabilities. What single trait, regardless of experience, is consistent among top performers?

There are many personal and professional traits or characteristics that may define a top performer and it can be hard to assign future success down to any single one trait, however I do see one consistency that really sticks out among the best. I personally believe it comes back to a person’s ability to command a network of high value relationships and bring people together in order to solve problems. This typically stems from a personality trait of curiosity and problem solving.

Their ability is to continuously probe and ask questions, to turn challenges that seem complex to an outsider into something simple they can understand. Our customers have not yet solved their respective issue and do not purchase solutions everyday, so if the account manager continuously searches for better ways to really get inside the mind of their buyer, they will be successful at moving the deal along. This kind of curiosity transforms an account manager/sales rep into a trusted advisor, as they align their knowledge of their solution or product with the buyers challenges throughout the purchasing journey.

3. Most of the inside sales process is typically automated for high-growth teams. What part of the inside sales process should NOT be automated?

We aren’t actually in a fully automated mode at Hootsuite when it comes to our sales process. Although it would be a fantastic as an organization to be able to automate everything, we have found that a personalized approach works best to start a conversation with a prospective customer, which may then lead into a future opportunity. Once a lead is nurtured and becomes an opportunity, the conversation is then led by the inside sales team. We do a lot to engage leads who have shown enough activity to indicate there’s potential interest, such as making a phone call, sending an email, connecting on LinkedIn or engaging on social media.

Account-based-marketing/selling is a priority for us now and is not “automatic” or “push button.” With a pre-studied and selected list of target accounts within a territory, you cannot wait for marketing to bring in leads. Target account selling is difficult to automate because it’s entirely proactive. Some of those accounts may not be actively searching for your solution right now, however you still need to start building that relationship long before they do. This requires focused proactive research, since account targets can represent great opportunity because of their size with potentially hundreds of buyers in each organization for your solution. It’s important for the account manager to have an appreciation of how big an opportunity may actually be for some of these accounts, and the amount of hard work that goes into creating and closing an Enterprise impact deal.

Key Takeaways

  • Inside sales was a relatively new route to market for medium to complex enterprise sales just 5 years ago. Prospects and customers are now inundated by inside sales teams with similar tactics. It’s critical that your reps understand this and that you set a higher standard to provide value with every outreach.
  • It’s very hard to determine future success by any one single personal and/or professional trait. However, top performers typically have an ability to ask customers the right questions in order to sole their challenges. This curiosity turns reps into trusted advisors that truly understand their buyers.
  • When account-based-marketing/selling is a priority, reps must proactively research and engage their target accounts. Since this process is entirely proactive, it’s very hard to automate.
The Challenger Sale: Taking Control of the Customer Conversation

The Challenger Sale: Taking Control of the Customer Conversation

What’s the secret to sales success? If you’re like most business leaders, you’d say it’s fundamentally about …
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Secrets to #InsideSales with @DDivecha Formerly @Eloqua Currently @Salesforce

1. You guided the inside sales team at Eloqua/Oracle from deal sizes as low as $18K ACV to well over $200K ACV. What was key to increasing deal sizes +1,000% from your inside sales reps?

We did this in a couple of ways:

  • Focusing on hiring sales reps with a specific profile that fit into the high growth environment. Instead of hiring reps with very little experience, we determined that reps with at least 2 years of SaaS selling experience worked best.
  • The revenue bar was raised every year or so. At the beginning we sold into accounts with annual revenues less than 20 million and gradually moved the bar up to 500 million. This allowed us to get into larger organizations who had more money to spend, hence larger deals.

2. You grew an inside sales team from 0 to 100+ people. What were some of the learnings in scaling your team to that size?

Continuously tweak the profile of the ideal rep you are trying to hire. As we started selling into larger organizations, it became necessary to hire more seasoned reps that could go on site to make presentations and meet the customer face to face.

Don’t hire in a hurry just to fill an open headcount. Look for the right candidate even if it takes a bit longer. “Bad breath is not necessarily better than no breath.” The cost of a bad hire could be as high as 2 years salary in some cases.

There will always be attrition when you’re in a growth mode, so keep a pool of potential candidates warm, in case you need to hire in a hurry. You should always be interviewing.

Managers need to continuously work on keeping sales reps motivated and happy, because with hyper-growth in the salesforce, the first thing that happens is territories shrink, and the manager needs to constantly work with the team to avoid any disruption or concerns with shrinking territories.

Get rid of bad apples fast, they can poison the entire barrel.

3. Most of the inside sales process is typically automated for high-growth teams. What part of the inside sales process should NOT be automated?

Training. There are tons of online training processes available today, however, certain aspects of training the sales team, like presentation skills, sales methodology (Sandler) etc. should be delivered in person – the other way doesn’t work. That’s the only one I can think of.

Key Takeaways

  • Focus on hiring sales reps with a specific profile that can seamlessly fit into a high growth environment. Growing deal sizes requires the revenue bar to be raised every year or so in order to establish a new, higher norm within the organization.
  • Hiring the ideal rep for your organization is a key driver of healthy growth. You must continuously tweak the profile of the ideal rep as your organization evolves. Don’t hire in a hurry – look for the right candidates to ensure long-term success and always be interviewing to plan for worst case attrition.
  • Training is one area of inside sales that will never be fully automated. Certain aspects of training the sales team, like presentation skills and sales methodologies, should be done in person.
SPIN Selling

SPIN Selling

Written by Neil Rackham, former president and founder of Huthwaite corporation, SPIN Selling is essential reading for …
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