Seeking Scale

Andy Baldacci and Craig Hewitt

A podcast about growing a SaaS business to meaningful scale

All Episodes

Craig and Andy talk about lessons they have learned in sales. Andy has minimal sales experience, while Craig has a ton of experience and continues to learn from others.  Craig shares how 90 days have passed since his new account executives were onboarded. The salespeople learned foundational things since they came in to break things and pull Castos in a new direction. Also, they have taught Craig a few things about effective sales strategies.   Andy, along with questions received from listeners, asks Craig for hiring guidance, the optimal way to sell a product, and salary plans for salespeople. Hire people aligned with the type of product you sell and sales philosophy/approach to succeed. Also, the price point dictates how much time to spend with customers and still be profitable for salespeople to make a living.  Don’t forget to read more about compensation and commission ratios on

Nov 30

32 min 36 sec

Craig and Andy talk about preparing to take time off as founders of growing businesses. When getting ready for a vacation or holiday, they need to wrap up, hand off, and document responsibilities at work.  Andy knows he needs to get a lot of little things done before Thanksgiving and going on his honeymoon. Some logistical things will just not get done and have to wait until he returns to the office. But he doesn’t expect to be completely unplugged and will be checking emails.  Craig has been working on his business and wants to work with SaaS-specific agencies to help with email marketing, content strategy, and other tasks. But it’s not a good time to start something new before taking time off from Christmas to New Years. He plans to be unavailable during that time and trusts his team to figure things out.

Nov 26

23 min 22 sec

Craig and Andy talk about building real, scalable companies that are not dependent on them as founders. Considering what they do with their time on a day-to-day basis is critical to grow.    Craig discusses how Castos had a really strong last month for sales. Now, he understands why forecasting and pipelines are really important. Craig likes to work a lot, but is he spending his time on the right, high-value tasks to accelerate growth? Andy explains how he is finding balance between working in or on his business. He has been making hiring decisions, but there’s still more positions to fill, manage, and grow. Revenue will predict when and who to hire for specific roles and responsibilities.  Also, when you get the right people in place and things start to work, it makes it all worth it.  

Nov 21

30 min 25 sec

Craig and Andy talk about executive assistants (EA), virtual assistants (VA), chief of staff (COS), and much more to get things delegated and done, oh my! Andy enjoyed gambling for work and taking a legitimate business expense for SaberSim at DraftKings – not all for not while living the dream. Also, Andy is working with Tim Francis from Great Assistant to find the right EA/VA because the goal is to work on the business and higher value things.  Craig has been having fun exploring customer acquisition channels and experimenting with a few different things to attract enterprise-type clients. Craig’s plan for Castos focuses on education and awareness of public and private podcasting by using the recently launched Automations Engine.  Also, Craig talked with Andrew Warner on Mixergy about private podcasting on the corporate side for internal podcasts as well as content/course creators and membership sites.

Nov 12

32 min 51 sec

Craig thinks everyone spends too much time, money, and effort on their products. Even extremely bad products can be incredibly successful. So, should focus be put on hiring more salespeople, marketers, or developers? Craig recommends reading, Radical Focus.  Craig updates listeners on how the two new AEs at Castos are two months in and doing really well. They are talking about optimizing a new channel. Craig is excited to see the growth and looking forward to much more of it. Andy sees the potential of adding bandwidth to develop partnerships that will succeed to better sell SaberSim products and serve customers. There’s a need to be deliberate and strategic in what is done in all areas of his business to decrease churn and diminished returns.

Oct 29

27 min 46 sec

Craig and Andy talk about whether they are ready to take the next step and control their own destiny by going from being individual contributors to leaders to build a bigger company faster. The problems are different, but don’t get easier as a company grows. For founders and CEOs, changing responsibilities involves enabling, empowering, and delegating more stuff to more people more often.  Craig updates listeners on Castos’s content marketing and SEO initiatives, including conversion optimization, lead nurturing, marketing to enable sales, and paid acquisition. For example, there’s an opportunity to take search results and traffic from blog posts to convert into trials. Andy is stuck doing admin tasks but has bigger and better things to do. Some things don’t seem important as other things, but they need to get done. Andy knows asking for help or hiring would be worthwhile for his company, SaberSim.

Oct 25

23 min 43 sec

How can a company double or triple its growth rate? Craig and Andy talk about ways to be more deliberate when it comes to scaling content marketing. Craig is ready to accelerate growth at Castos. His options include content and SEO as well as paid acquisition – all of which Castos does already and both have been successful to an extent. How does he move forward with those options – more, less, or different ways to affect growth?  Andy’s approach is to identify the pitfalls of growth. Rather than going through the motions, be strategic about what to work on, how to do it, and reasons why. Do more of what is already working. It takes bandwidth and experience to make an impact and transform a business.

Oct 18

19 min 10 sec

Craig and Andy revisit the quality assurance (QA) process, as well as talk about sales and marketing hires to add bandwidth and balance priorities. Craig provides an update on hiring an internal QA person or external agency. The best way to QA is in the development process with unit and integration tests. Instead of hiring a person, development resources will be devoted to improving test coverage, especially for critical paths.  Craig will document and record how to test new features, then user acceptance testing will be conducted by his team on Castos’ testing site before it gets to staging. Castos has three environments: Production, Test, and Staging.  However, Andy encourages Craig to have a product owner write and communicate the specs. Also, Andy’s team is pushing for unit tests because they have none. It’s always an issue when things are released and something breaks. Better testing is one of Andy’s priorities.

Oct 11

27 min 59 sec

Craig and Andy talk about the need for an in-house or external quality assurance (QA) agency to grow a business and team that plans for unexpected consequences and interactions.  Currently, Craig is in the midst of a team retreat and identifying the need for a QA solution. There is no plan, documentation, or accountability for how something is tested before it is launched, shipped, or pushed out. Do you think it’s good? Do you think it’s ready? Is it safe? Passing the buck is not okay.   Andy prioritizes team roles and responsibilities differently to define the product process. It may not be the best path to follow because it’s better to be thorough and expect some hands-on feedback. Rather than add people and complexity that slows things down, don’t sweat the details. Sometimes, there can be too many cooks in the kitchen to take things off your plate to fulfill the order.

Oct 4

33 min 25 sec

Andy and Craig talk about being busy and a lot going on like always. But some of the parts of the business seemed slow, especially for Andy. It took a lot of focus, discipline, and the right team to get something done right. Andy reports on the refactor/redesign rollout and pricing updates of SimSaber’s Daily Fantasy Sports (DFS) app for football season. There was a false start the first few months, but working closely with developers and designers to get an end date and ship the new version of the app was worth the wait.  Now, the app has added functionality, features, and works much better, especially for user experience. The redesign launch with pricing updates went as well as it could have with no major performance issues. It helps significantly with conversions, retention rates, and ROI. Craig agrees that raising prices on current customers generally goes well because they get a lot of value out of the product. With new customers, they know Castos is the best place for their podcasts. The more successful their show is, the more marketing features they should unlock. As their show grows, Castos’s functionality grows with them.

Sep 27

32 min 31 sec

Andy and Craig talk about what if you wake up every morning, ready to do your job? Once you cross the finish line and get big things done, do you need to do retrospectives and post-mortems of projects to be successful? Craig’s teams do them after every sprint and they consist of discussing what do you want to start doing, stop doing, and do more of? Then, take action, prioritize, and tackle projects.  Andy has taken a waterfall or agile approach to get everyone’s opinion and accept feedback. The key is to be more strategic and make changes by hiring the right people, especially once the craziness of football season subsides. Growth Goal: If you don’t have time to get work done, hire specialists who can move forward. More people can get more things done, however, delegating trust to do things can make coordination and communication more difficult to move in the right direction.

Sep 20

28 min 31 sec

Andy and Craig talk about taking time off to unplug from the business, delegating tasks and responsibilities, and holding team retreats. Andy knows he doesn’t have to delegate everything or worry when he goes away for a few days or on a business trip. He knows someone will notify him if something goes seriously wrong.  Craig agrees. His goal is to take the week between Christmas and New Year’s off. From a sales perspective, nothing gets done and developers take time off and don’t release new features. Also, Craig is organizing a virtual team retreat that will focus on setting and tracking objectives and key results (OKRs) at the company, team, and individual levels. People will get to know each other better and get out of the normal day-to-day work environment.  Both Craig and Andy know it’s important for all team members to understand why things are done and offer feedback.

Sep 13

33 min 45 sec

Andy and Craig provide updates on refactoring, redesigning, rebranding, and releasing new versions of their websites and web apps. Andy has been working on a big redesign at SaberSim and plans to publicly release the new version of the app soon. It has taken a lot of time, tweaks, and improvements to get it right. Andy expects the app’s new features and functionality to affect conversion rates and churn.  Craig is taking a more iterative approach to rebranding his business, Castos. It will include a new logo, colors, fonts, themes, and layouts. It’s much more manageable to make changes on the marketing website, but the brand’s look and feel will be carried through to the web app.

Sep 6

20 min 4 sec

Risks and Efforts vs. Results: Andy and Craig talk about sales onboarding tools and delegating task-level work.  According to Andy, it’s a forcing function to focus as football season starts and build winning lineups with SaberSim. When deadlines loom, he figures out and delegates what doesn’t matter or needs to get done right now. What matters is an upcoming launch revealing a new design and functionality! Craig has had a busy week, as well. Two sales reps have been onboarded to help them understand processes, procedures, and documentation — only to come in with new ideas and challenge the status quo at Castos. 

Aug 30

19 min 9 sec

Andy and Craig talk swag for team members, customers, and partners. What’s the purpose of it? Where and on whom should startups spend money to be successful? Craig shares how Castos created swag with a simple slogan in the form of T-shirts and hoodies for team members in the past using Printful. Also, he plans to add and send some more really nice swag such as water bottles and food for a rebranding project with the new logo for team members as well as specific customers.  Craig leverages and coordinates partnerships, product integrations, marketing co-promotions, affiliates, and customers to recommend and promote Castos to other people and businesses.  Andy recalls Hiten Shah encouraging businesses to buy better swag. The cost difference is minimal. For all the shirt swag that Andy has done, it’s been higher quality and comfortable. Swag is not only for marketing purposes, including to win contests on DraftKings or FanDuel, but for people to proudly wear and display it.  Andy discusses how SaberSim spends about five-figures a year on swag, but it is more for customers, especially for those in the United States – not standard to ship internationally.

Aug 16

46 min 29 sec

Craig and Andy talk about how the concept of deep versus wide can apply to every aspect of your life and business. Do you do a bunch of things? Does your app have lots of features and serve different types of people, or is it the best at one specific thing? Andy and Craig share different perspectives when it comes to products and marketing challenges. Craig covers the wide side with Castos doing everything, while Andy focuses deeply on doing, executing, and sticking with one thing.  Andy wants to take Sabersim wider, too. It’s getting ready for football by locking in a team, capitalizing on maintaining the team if revenue stays the same, and planning for significant growth. Andy is ambitious and wants to grow quickly, but doesn’t deal well with the stress of it.  Craig enjoys working a solid six hours a day and taking more time to spend with his family. He doesn’t feel guilty, but good about that balance. He describes raising money and hiring people as expanded focus with more ability to focus and more things to focus on to be successful.

Aug 9

36 min 59 sec

Craig and Andy talk about the peaks and valleys of seasons from a business perspective. They discuss the importance of being intentional and deliberate to make progress and remain profitable. After taking time to recharge, it’s time to get back to work. During the summer, Craig has been working less. Being intentional and taking microsteps makes him more efficient. Craig uses the Things app and continues to implement the Entrepreneurial Operating System (EOS) using Traction.   Morning is Andy’s most productive time, and then he tends to lose energy. He finds being deliberate about planning and shifting things helps him to deliver progress. Andy uses Trello, but struggles to stay focused when business is slow. All that changes when fall sports start up.

Aug 2

32 min 23 sec

Craig and Andy talk about taking time off, finding ways to recharge, and balancing their well-being by hiring resources to grow and move their businesses forward. Craig had a difficult time finding and hiring a front-end developer. But he did make an offer to a female developer in Chile that was accepted. She will start on Aug. 1. She will mold her mad skills and experiences to existing processes at Castos.   Also, Craig made offers to two account executives, which was a much more straightforward process. Simply set clear expectations and goals for sales and planning leads. Andy knows and understands how difficult it is to bring on somebody to do something you have not done before. Working with contractors and agencies during a test phase can be super valuable. However, when should you increase the budget and take time to hire someone?

Jul 26

25 min 55 sec

Craig and Andy talk about how and when they do strategic planning to grow their businesses. Craig tries to strike a balance between planning to strategically get work done. Although he tends to spend time planning and working, Craig needs to consistently relay and communicate strategic plans to make leaders and team members aware of future goals for growth. Currently, Craig is strategically planning to hire more salespeople by working backwards from revenue goals for the next 12 months by product, commission, and schemas.  Andy also has revenue goals that are not really based on anything. Instead, he focuses on product opportunities, improvements, content, resources, and what needs to get done by when. Being different from other brands and competitors is the key to growth without losing focus. 

Jul 19

35 min 14 sec

Craig and Andy talk about creating alternative content to communicate with customers and community as the silver bullet to success. Make it meaningful and valuable. Andy embraces the MVP mentality to engage customers and offer support via office hours, FAQs, videos, documentation, and other content. Also, strategy sessions offer a deeper dive into specific subjects to build content and relationships with customers and community. Craig discusses how Castos offers call sessions with potential and existing customers to increase engagement and offer support to be more successful with podcasting. Also, Craig is in the process of working with Blue Coding, a developer placement agency. Adding team members in the same time zone allows for live meetings and calls. However, hiring isn’t easy and being asynchronous continues to be a challenge.

Jul 12

29 min 22 sec

In this episode, Andy and Craig talk about the recent fundraising round that Craig closed at Castos. There are lots of lessons learned in the fundraising process, and now that the round is closed Andy and Craig explore how Castos will put these new financial resources to work. In this episode Andy and Craig talk about: The process of fundraisingValuation and corporate partners involvedHow the resources will be allocatedWhat the hiring steps are for CastosDriving the sales organization. Resources Mentioned: Castos’ Fundraising Announcement

Jul 5

36 min 37 sec

Craig and Andy talk about hiring for sales, support, and other roles. Dealing with what they don’t know involves hiring great people with the right strengths and skills.  Andy shares how business travel has made him fall behind on day-to-day work, but he is still able to oversee high-level progress. He is going to take a step back and stay home to get some work done. Also, Andy plans to hire a virtual assistant (VA) for marketing administration support.   In just one month, Craig hired two developers and two support people. Unfortunately, one of the support specialists did not work out. Craig’s advice and solution – review hiring, screening, and interview process. Always check job references!

Jun 28

30 min 35 sec

Craig and Andy talk about meetings and team dynamics. When there’s so much going on, it’s difficult to gain clarity and be productive and effective.   Andy discusses how finding a rhythm for meetings helps to structure the company. It’s still a work in progress. Andy has brief stand-up to longer sit-down and detailed meetings with specific team members. Also, he blocks out time for specific tasks to avoid distractions. However, when unexpected things happen, it can be difficult to get back on track and catch up.  Craig talks about the challenge of coordinating and collaborating with internal and external teams that work remotely. Although team members work all hours of the day and all over the world, the goal is to be as asynchronous as possible.  Be honest to be kind to others and create a connection. Craig recommends reading, Radical Candor – Be a Kick-Ass Leader and Empower Your Team.

Jun 7

30 min 9 sec

Out of office – what will break if or when you are away? Nobody wants to be a micromanager or be told what to do. Craig and Andy talk about how and what they plan to do to be better managers and lead their teams.  You know you’re getting older when you want to leave Las Vegas and get back home to sleep and get over a hangover. So, Andy’s back in the office and looking to delegate more for the next time he checks out for a few days to come back and not much needs to be done or fixed. Craig is also looking forward to taking a week off during the summer. But before then, he needs to not get involved in things that don’t need his attention and time. His team will tell him, ‘We got this, go do something else!’ According to Craig, being a fun and effective manager is an asset, but it’s easy to be a jerk and  dictatorial manager. Empower your team by identifying priorities and setting realistic goals. What have you done this week and was it worth your time?

May 31

34 min 37 sec

Craig and Andy talk about making progress by providing onboarding updates for new employees and customers.  Craig discusses improving the onboarding process and sequence for employees, which includes Sam, the new Head of Growth. He will start on Monday and brings senior-level experience generating revenue.   As for onboarding customers, Craig has had challenges. Once some people sign up for Castos, they are not engaging or getting started. The problem is figuring out, why? Will live chat from Zendesk and an onboarding checklist from Hopscotch help?  Andy suggests possible ways to help onboard customers, such as offer office hours and one-on-one support. Rather than focusing on ‘how’ to do something, provide ‘what’ to do next.  Andy is not quite ready to develop an extensive and intentional onboarding process for new employees, but is making progress with content planning and process work.  

May 24

22 min 51 sec